From 9d9686835106fd31cbc6028a11e174cb23006cb4 Mon Sep 17 00:00:00 2001 From: Jose Pablo Folch <70032477+jpfolch@users.noreply.github.com> Date: Fri, 13 Mar 2026 16:53:03 +0000 Subject: [PATCH 1/8] Adding Catechol Dataset (#233) * Added catechol dataset pbtxt * fixed yields * changes from review * actual review changes, removal of template --- catechol_dataset_ord.pbtxt | 374237 ++++++++++++++++++++++++++++++++++ 1 file changed, 374237 insertions(+) create mode 100644 catechol_dataset_ord.pbtxt diff --git a/catechol_dataset_ord.pbtxt b/catechol_dataset_ord.pbtxt new file mode 100644 index 0000000..80d41a1 --- /dev/null +++ b/catechol_dataset_ord.pbtxt @@ -0,0 +1,374237 @@ +name: "catechol_dataset" +description: "Dataset for catechol reactions" +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "1" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "1.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "CO" + } + identifiers { + type: NAME + value: "Methanol" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "OCCO" + } + identifiers { + type: NAME + value: "Ethylene Glycol [1,2-Ethanediol]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 2.001019 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=CC=C1CC=C" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 2" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 90.311775 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "1" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "2.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "CO" + } + identifiers { + type: NAME + value: "Methanol" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "OCCO" + } + identifiers { + type: NAME + value: "Ethylene Glycol [1,2-Ethanediol]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 3.9781666 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=CC=C1CC=C" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 2" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 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datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 10.03113 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 87.68018 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "1" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "5.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "CO" + } + identifiers { + type: NAME + value: "Methanol" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "OCCO" + } + identifiers { + type: NAME + value: "Ethylene Glycol [1,2-Ethanediol]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 13.0792265 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 1.3466706 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 85.75853 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "1" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "6.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.011731 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.006811 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "2" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 82.60241 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "2" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "5.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.15682231 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 4.111122 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 81.930084 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "2" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "6.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.16507633 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 7.1216145 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 76.8009 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "2" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "12.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.995884 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 7.2403936 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 76.35705 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "2" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "13.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.001417 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 68.9272 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "2" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "19.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 15.690018 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 69.13286 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "2" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "20.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "3" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "3" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 11.273508 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 11.224875 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 77.60105 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "3" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "6.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "CO" + } + identifiers { + type: NAME + value: "Methanol" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "OCCO" + } + identifiers { + type: NAME + value: "Ethylene Glycol [1,2-Ethanediol]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.292628 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 15.002037 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 71.29965 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "3" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "7.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.009928 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "4" + } + 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.0043745 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 70.30777 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "4" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 76.81182 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "4" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "6.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 6.736646 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 77.44719 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "4" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "7.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "4" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.993313 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 3.831644 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 82.42822 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "4" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "13.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.16507633 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.997922 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 3.8353598 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 82.80083 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "4" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "14.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.16507633 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.004088 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.009681 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "4" + } + 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 85.422485 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "4" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "20.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 1.5297463 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 85.462776 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "4" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "21.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 37.75908 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "5" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "6.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Temperature Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "CO" + } + identifiers { + type: NAME + value: "Methanol" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "OCCO" + } + identifiers { + type: NAME + value: "Ethylene Glycol [1,2-Ethanediol]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 203.4589 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 22.10174 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 14.901103 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "5" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "7.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Temperature Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 212.88292 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "5" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 3.5012846 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "5" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "13.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Temperature Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 3.05894 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "6" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "1.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "6" + } + 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 2.001019 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 73.2139 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "6" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.011946 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 5.7000685 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "7" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "1.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "CO" + } + identifiers { + type: NAME + value: "Methanol" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "OCCO" + } + identifiers { + type: NAME + value: "Ethylene Glycol [1,2-Ethanediol]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.00708 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 28.597189 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 4.508197 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "7" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "2.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.0005735322 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.000857 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "7" + } + 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "7" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "8.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.16507633 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 38.656017 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "7" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "9.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.19397672 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "7" + } + 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.23365147 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.98855 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "7" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.001147 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "7" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "15.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.39002028 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.0121 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 52.279766 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "7" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "16.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.42853326 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.015312 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "7" + } + 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.46709776 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.016965 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "7" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "8" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "2.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "CO" + } + identifiers { + type: NAME + value: "Methanol" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "OCCO" + } + identifiers { + type: NAME + value: "Ethylene Glycol [1,2-Ethanediol]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 3.968719 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 51.00291 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 5.0507073 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "8" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "3.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 7.00235 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "8" + } + 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 10.036129 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 52.68279 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "8" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "9" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "3.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.45884058 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.995206 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 52.126415 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "9" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.42021346 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.9914255 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "9" + } + 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.38163805 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.989209 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "9" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "9" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "10.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.26439407 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988553 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 45.26399 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "9" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "11.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.22473228 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.989431 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "9" + } + 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.18508817 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.99187 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "9" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 34.016483 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 4.3599043 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "9" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "17.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.06956802 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.01543 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 24.890282 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 6.0431786 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "9" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "18.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[1,2-Ethanediol]" + } + amount { + volume { + value: 0.031000976 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017006 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "1" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "9" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 2.001019 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 2.5191119 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 95.78332 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "10" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "2.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "C(C(F)(F)F)(C(F)(F)F)O" + } + identifiers { + type: NAME + value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O1C(C)CCC1" + } + identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 3.9728506 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=CC=C1CC=C" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 2" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 7.0948215 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 9.65714 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 83.24805 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "10" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "3.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 7.006481 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 57.927853 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "10" + } + 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identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 10.04026 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "10" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.000545 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 35.62873 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "11" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "3.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "C(C(F)(F)F)(C(F)(F)F)O" + } + identifiers { + type: NAME + value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" + } + amount { + volume { + value: 0.45878792 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O1C(C)CCC1" + } + identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.041212067 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.9952 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=CC=C1CC=C" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 2" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 22.410843 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 28.374292 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 41.09423 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "11" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.079839125 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.991422 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "11" + } + 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identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.118414454 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.989207 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 24.093227 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "11" + } + 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 80.47101 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "11" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "10.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "C(C(F)(F)F)(C(F)(F)F)O" + } + identifiers { + type: NAME + value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" + } + amount { + volume { + value: 0.26434004 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O1C(C)CCC1" + } + identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.23565996 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988553 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=CC=C1CC=C" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 2" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 4.990735 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 8.73737 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 86.072685 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "11" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "11.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.27532172 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.989433 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "11" + } + 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.991875 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 4.6635056 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "11" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.0123005 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 1.5291871 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 89.20325 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "11" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "17.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "C(C(F)(F)F)(C(F)(F)F)O" + } + identifiers { + type: NAME + value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" + } + amount { + volume { + value: 0.069515534 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O1C(C)CCC1" + } + identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.43048447 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.015433 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=CC=C1CC=C" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 2" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 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datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 1.0676368 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 89.02098 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "11" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "18.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 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NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.4690516 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017007 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "11" + } + identifiers { + 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "12" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "3.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "C(C(F)(F)F)(C(F)(F)F)O" + } + identifiers { + type: NAME + value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O1C(C)CCC1" + } + identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 5.200749 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 1.2651249 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "12" + } + identifiers { + 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NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 8.234417 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "12" + } + identifiers { + 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NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 11.268191 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.81140405 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 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datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.8408241 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 87.752365 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "13" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "3.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "C(C(F)(F)F)(C(F)(F)F)O" + } + identifiers { + type: NAME + value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" + } + amount { + volume { + value: 0.056853067 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O1C(C)CCC1" + } + identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.44314694 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.993482 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=CC=C1CC=C" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 2" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.24210116 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 1.2346823 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 87.93605 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "13" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.40454084 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.990336 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "13" + } + 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identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.3659864 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988755 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "13" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 83.91733 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "13" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "10.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "C(C(F)(F)F)(C(F)(F)F)O" + } + identifiers { + type: NAME + value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" + } + amount { + volume { + value: 0.25171566 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O1C(C)CCC1" + } + identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.24828434 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988722 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=CC=C1CC=C" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 2" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 10.220742 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 16.638145 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 74.73329 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "13" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "11.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.20862973 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.990233 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "13" + } + 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identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.16899282 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.993306 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "13" + } + 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "13" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.013757 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 32.452816 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 38.046383 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "13" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "17.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "C(C(F)(F)F)(C(F)(F)F)O" + } + identifiers { + type: NAME + value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" + } + amount { + volume { + value: 0.44608876 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O1C(C)CCC1" + } + identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.05391125 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.016259 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=CC=C1CC=C" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 2" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 27.151543 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 34.33017 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 34.103275 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "13" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "18.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.015323232 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.0172 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "13" + } + 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 31.844116 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "14" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "3.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Temperature Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "C(C(F)(F)F)(C(F)(F)F)O" + } + identifiers { + type: NAME + value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O1C(C)CCC1" + } + identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 178.54456 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 37.262783 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 20.87241 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "14" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Temperature Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 184.32751 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "14" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "14" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "10.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Temperature Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "C(C(F)(F)F)(C(F)(F)F)O" + } + identifiers { + type: NAME + value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O1C(C)CCC1" + } + identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 27.947672 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "14" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "11.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Temperature Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 3.828392 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 41.14162 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 3.4187799 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "15" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "C(C(F)(F)F)(C(F)(F)F)O" + } + identifiers { + type: NAME + value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O1C(C)CCC1" + } + identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 6.8620224 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=CC=C1CC=C" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 2" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 38.88315 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 31.447828 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "15" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "5.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "C(C(F)(F)F)(C(F)(F)F)O" + } + identifiers { + type: NAME + value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O1C(C)CCC1" + } + identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 9.895796 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "15" + } + 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identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 12.929456 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 26.124445 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "15" + } + 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.995419 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 30.357801 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "16" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "C(C(F)(F)F)(C(F)(F)F)O" + } + identifiers { + type: NAME + value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" + } + amount { + volume { + value: 0.4219991 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O1C(C)CCC1" + } + identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.07800091 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.991566 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=CC=C1CC=C" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 2" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 36.411766 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 40.413925 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 10.404336 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "16" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "5.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.116578706 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.989277 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "16" + } + 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identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.15510488 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "16" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.98855 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 42.87976 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 7.5184293 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "16" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "11.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "C(C(F)(F)F)(C(F)(F)F)O" + } + identifiers { + type: NAME + value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" + } + amount { + volume { + value: 0.22656652 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O1C(C)CCC1" + } + identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.27343348 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.989356 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=CC=C1CC=C" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 2" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 38.196968 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 44.36345 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 12.500701 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "16" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "12.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "C(C(F)(F)F)(C(F)(F)F)O" + } + identifiers { + type: NAME + value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" + } + amount { + volume { + value: 0.18692161 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O1C(C)CCC1" + } + identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.3130784 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.991723 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "16" + } + 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 43.662384 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "16" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.01532 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 28.330223 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 15.282176 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "16" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "18.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "C(C(F)(F)F)(C(F)(F)F)O" + } + identifiers { + type: NAME + value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" + } + amount { + volume { + value: 0.032786116 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O1C(C)CCC1" + } + identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.4672139 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.016968 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=CC=C1CC=C" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 2" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 30.834179 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 20.647411 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 19.989378 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "16" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "19.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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+ type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 5.05629 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 10.619443 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 50.141273 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "17" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "C(C(F)(F)F)(C(F)(F)F)O" + } + identifiers { + type: NAME + value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O1C(C)CCC1" + } + identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 8.089946 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=CC=C1CC=C" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 2" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 25.141245 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 14.805421 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 33.88894 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "17" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "5.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "C(C(F)(F)F)(C(F)(F)F)O" + } + identifiers { + type: NAME + value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O1C(C)CCC1" + } + identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 11.123731 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "17" + } + 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identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.157308 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 17.520384 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "17" + } + 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.99367 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 38.035 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 12.697185 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "18" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "C(C(F)(F)F)(C(F)(F)F)O" + } + identifiers { + type: NAME + value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" + } + amount { + volume { + value: 0.13217884 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O1C(C)CCC1" + } + identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.36782116 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988795 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=CC=C1CC=C" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 2" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 38.875973 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 45.754852 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 8.768627 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "18" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "5.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "18" + } + 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "18" + } + 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.990127 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 42.777637 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "18" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "11.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "C(C(F)(F)F)(C(F)(F)F)O" + } + identifiers { + type: NAME + value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" + } + amount { + volume { + value: 0.32912013 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O1C(C)CCC1" + } + identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.17087989 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.993124 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=CC=C1CC=C" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 2" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 37.34968 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 42.676105 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 2.2539942 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "18" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "12.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.16507633 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.997683 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "18" + } + 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.003771 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "18" + } + 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "18" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "18.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "C(C(F)(F)F)(C(F)(F)F)O" + } + identifiers { + type: NAME + value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O1C(C)CCC1" + } + identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 27.140732 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "18" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "19.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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+ type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "2" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "18" + } + 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+ type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 92.144005 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "19" + } + identifiers { + 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 7.002725 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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-6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 92.25244 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "19" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "C1CCCCC1" + } + identifiers { + type: NAME + value: "Cyclohexane" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CC(O)C" + } + identifiers { + type: NAME + value: "IPA [Propan-2-ol]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 10.036504 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 88.88638 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "19" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "5.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 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+ volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 13.070155 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 87.48093 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "19" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "6.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.011744 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 86.734474 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "20" + } + identifiers { + 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1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "20" + } + identifiers { + type: 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 86.68076 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.9914255 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 88.08293 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "20" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "5.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "C1CCCCC1" + } + identifiers { + type: NAME + value: "Cyclohexane" + } + amount { + volume { + value: 0.38163328 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CC(O)C" + } + identifiers { + type: NAME + value: "IPA [Propan-2-ol]" + } + amount { + volume { + value: 0.118366726 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.989209 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=CC=C1CC=C" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 2" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.46019408 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.6154301 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 89.519035 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "20" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "6.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Propan-2-ol]" + } + amount { + volume { + value: 0.15689051 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 90.78004 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "20" + } + 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[Propan-2-ol]" + } + amount { + volume { + value: 0.16507633 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 90.73918 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "20" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.989431 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 94.65057 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "20" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "12.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Propan-2-ol]" + } + amount { + volume { + value: 0.31491673 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.991871 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 1.0521514 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 95.11854 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "20" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "13.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Propan-2-ol]" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.99587 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 95.324486 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "20" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "14.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Propan-2-ol]" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.001429 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 1.2703363 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 95.71138 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "20" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.014551 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 1.5631973 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 96.7592 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "20" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "19.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Propan-2-ol]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.011199 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 1.6133546 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 96.84827 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "21" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "1.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Propan-2-ol]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.006083 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 96.97397 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "21" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "2.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Propan-2-ol]" + } + amount { + volume { + value: 0.49253884 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.999777 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 1.4789124 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 97.09766 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "21" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 95.51322 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "21" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "7.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Propan-2-ol]" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 1.0617535 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 95.54551 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "21" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "8.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Propan-2-ol]" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 94.82092 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "21" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "9.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Propan-2-ol]" + } + amount { + volume { + value: 0.29896262 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 94.69428 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "21" + } + 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amount { + volume { + value: 0.16507633 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.996497 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 92.43759 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "21" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "14.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "C1CCCCC1" + } + identifiers { + type: NAME + value: "Cyclohexane" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CC(O)C" + } + identifiers { + type: NAME + value: "IPA [Propan-2-ol]" + } + amount { + volume { + value: 0.16507633 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.002256 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=CC=C1CC=C" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 2" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.3270392 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 92.0311 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "21" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "15.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "C1CCCCC1" + } + identifiers { + type: NAME + value: "Cyclohexane" + } + amount { + volume { + value: 0.35839972 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CC(O)C" + } + identifiers { + type: NAME + value: "IPA [Propan-2-ol]" + } + amount { + volume { + value: 0.14160028 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.008292 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "21" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "16.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 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amount { + volume { + value: 0.10312963 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.012786 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 88.73408 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "21" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "17.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 82.71462 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "21" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "21.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 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volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 83.795456 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "22" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "1.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Temperature Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 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amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "2.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Temperature Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 83.52969 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 54.331802 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "22" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "7.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Temperature Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "C1CCCCC1" + } + identifiers { + type: NAME + value: "Cyclohexane" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CC(O)C" + } + identifiers { + type: NAME + value: "IPA [Propan-2-ol]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 211.31673 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 39.980015 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "22" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "8.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Temperature Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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[Propan-2-ol]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 218.31372 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 31.619055 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "22" + } + 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[Propan-2-ol]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "22" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 24.906404 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "22" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "14.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Temperature Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "C1CCCCC1" + } + identifiers { + type: NAME + value: "Cyclohexane" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CC(O)C" + } + identifiers { + type: NAME + value: "IPA [Propan-2-ol]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 8.362453 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 25.289581 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "22" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "15.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Temperature Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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[Propan-2-ol]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017031 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 22.925522 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "22" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "16.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Temperature Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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[Propan-2-ol]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.015502 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 7.6807146 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 23.910723 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "22" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.995988 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 26.10105 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "23" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "3.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Propan-2-ol]" + } + amount { + volume { + value: 0.073357075 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.991946 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 28.758564 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 24.188576 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "23" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Propan-2-ol]" + } + amount { + volume { + value: 0.11194108 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.98947 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 23.630808 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "23" + } + 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[Propan-2-ol]" + } + amount { + volume { + value: 0.15047346 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988555 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 33.827362 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 24.591888 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "23" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 20.562538 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "23" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "10.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Propan-2-ol]" + } + amount { + volume { + value: 0.26866356 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.989177 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 40.971825 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 18.968412 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "23" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "11.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Propan-2-ol]" + } + amount { + volume { + value: 0.3083106 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.991356 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 19.074432 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "23" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "12.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Propan-2-ol]" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.995094 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 40.278557 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 18.87398 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "23" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.0147295 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 13.996451 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "23" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "17.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Propan-2-ol]" + } + amount { + volume { + value: 0.4626002 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.014837 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 42.852303 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 13.341183 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "23" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "18.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Propan-2-ol]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.0119 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 13.331798 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "24" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "1.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Propan-2-ol]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.007044 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=CC=C1CC=C" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 2" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 41.81357 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 43.63048 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 14.112561 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "24" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.9892645 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 18.425726 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "24" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "6.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Propan-2-ol]" + } + amount { + volume { + value: 0.34457612 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 40.49446 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 18.48394 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "24" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "7.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Propan-2-ol]" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 18.817009 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "24" + } + 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[Propan-2-ol]" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 38.967728 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 19.89236 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "24" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.991749 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 24.187658 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "24" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "13.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Propan-2-ol]" + } + amount { + volume { + value: 0.16507633 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.995688 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 35.09597 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 23.70262 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "24" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "14.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Propan-2-ol]" + } + amount { + volume { + value: 0.16507633 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.001188 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 24.613047 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "24" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "15.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Propan-2-ol]" + } + amount { + volume { + value: 0.14800707 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.007392 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 29.051403 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 25.573639 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "24" + } + 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 26.47246 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "24" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "20.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Propan-2-ol]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 23.539667 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "24" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "21.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Propan-2-ol]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "3" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "24" + } + 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "25" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 84.46417 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "25" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "5.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "O.CC#N" + } + identifiers { + type: NAME + value: "Water.Acetonitrile" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CC#N" + } + identifiers { + type: NAME + value: "Acetonitrile" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 13.07732 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 10.575115 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 75.351036 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "25" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "6.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.011753 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "26" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 87.619125 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "26" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "6.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile" + } + amount { + volume { + value: 0.15698144 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 5.690413 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 88.49821 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "26" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "7.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile" + } + amount { + volume { + value: 0.16507633 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "26" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.9918785 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 95.93497 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "26" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "13.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.995881 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 2.3298657 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 95.83212 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "26" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "14.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.001443 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "26" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.007615 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 97.16668 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "26" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "26" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "20.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 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volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 99.50125 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "26" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "21.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 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volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "27" + } + identifiers { + 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "27" + } + identifiers { + 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 11.257154 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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-7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 99.0432 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "27" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "6.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 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amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.305167 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 99.00549 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "27" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "7.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 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amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.009931 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "28" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "1.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.004378 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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-7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 99.0256 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "28" + } + identifiers { + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 95.95616 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "28" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "6.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 2.5049632 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 95.887856 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "28" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "7.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "28" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.993292 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 87.68716 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "28" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "13.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile" + } + amount { + volume { + value: 0.16507633 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.997918 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 5.71842 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 87.87429 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "28" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "14.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile" + } + amount { + volume { + value: 0.16507633 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.004054 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "28" + } + 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 74.79351 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "28" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 74.75508 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "28" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 6.7943544 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "29" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 203.48334 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "29" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 212.90666 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "29" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "30" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "30" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "7.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "O.CC#N" + } + identifiers { + type: NAME + value: "Water.Acetonitrile" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CC#N" + } + identifiers { + type: NAME + value: "Acetonitrile" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.011949 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 39.328926 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "31" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "1.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "31" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "31" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "7.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile" + } + amount { + volume { + value: 0.16507633 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 33.70682 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "31" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "8.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile" + } + amount { + volume { + value: 0.16507633 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "31" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.995655 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 1.1716859 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "31" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "14.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.001113 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 32.09876 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 2.298289 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "31" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "15.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile" + } + amount { + volume { + value: 0.35171765 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.007353 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "31" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 14.01071 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "31" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 14.344561 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "32" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "1.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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"Acetonitrile" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "32" + } + 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 2.011623 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 84.29281 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "32" + } + 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.160716 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 15.573803 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 14.566842 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "32" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "7.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "O.CC#N" + } + identifiers { + type: NAME + value: "Water.Acetonitrile" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CC#N" + } + identifiers { + type: NAME + value: "Acetonitrile" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.010179 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 15.438672 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 14.855659 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "33" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "1.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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+ } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.004679 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "33" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.94460833 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "33" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "7.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 32.980995 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.51529515 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "33" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "8.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile" + } + amount { + volume { + value: 0.32966438 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "33" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 31.924952 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "33" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.997688 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 31.867237 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "33" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "14.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile" + } + amount { + volume { + value: 0.16507633 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.003778 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 32.959305 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "33" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "15.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile" + } + amount { + volume { + value: 0.1327207 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.009468 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "33" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "33" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "33" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "4" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "33" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "22.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 99.82308 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "34" + } + identifiers { + type: 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 13.075269 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "34" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "6.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "CC#N" + } + identifiers { + type: NAME + value: "Acetonitrile" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CC#N.CC(=O)O" + } + identifiers { + type: NAME + value: "Acetonitrile.Acetic Acid" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.011737 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 99.54359 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "35" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "1.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 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amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.006818 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "35" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "2.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 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Acid" + } + amount { + volume { + value: 0.0025504953 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.000543 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "35" + } + identifiers { + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 96.84097 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "35" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "7.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile.Acetic Acid" + } + amount { + volume { + value: 0.16507633 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.9451746 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 97.201614 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "35" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "8.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile.Acetic Acid" + } + amount { + volume { + value: 0.16507633 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "35" + } + 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 92.9885 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "35" + } + 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"Acetonitrile.Acetic Acid" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.001439 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 92.34244 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "35" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "15.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile.Acetic Acid" + } + amount { + volume { + value: 0.353522 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.007611 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "35" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.012302 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "35" + } + 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 87.86779 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "36" + } + 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"Acetonitrile.Acetic Acid" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 98.94947 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "36" + } + identifiers { + type: 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 88.22367 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "36" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "7.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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"Acetonitrile.Acetic Acid" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.009956 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 2.9275134 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 88.11197 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "37" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "1.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile.Acetic Acid" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.004383 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.99819 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "37" + } + 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 93.24159 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "37" + } + 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"Acetonitrile.Acetic Acid" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 93.60018 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "37" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "8.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile.Acetic Acid" + } + amount { + volume { + value: 0.32761297 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "37" + } + 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 97.48715 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "37" + } + 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"Acetonitrile.Acetic Acid" + } + amount { + volume { + value: 0.16507633 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.00408 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 98.20769 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "37" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "15.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile.Acetic Acid" + } + amount { + volume { + value: 0.13091536 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.009697 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.013758 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "37" + } + identifiers { + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "37" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "21.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 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amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 99.5805 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "38" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "1.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Temperature Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 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Acid" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 44.477066 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "38" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "7.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Temperature Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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"Acetonitrile.Acetic Acid" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 213.23158 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 24.937365 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "38" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "8.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Temperature Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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"Acetonitrile.Acetic Acid" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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"Acetonitrile.Acetic Acid" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 15.23414 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "39" + } + 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"Acetonitrile.Acetic Acid" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 2.001019 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "39" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 15.661898 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "40" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "1.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile.Acetic Acid" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.007088 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 15.785672 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 15.597706 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "40" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "2.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile.Acetic Acid" + } + amount { + volume { + value: 0.0007073492 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.000835 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.995417 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "40" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "40" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "8.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile.Acetic Acid" + } + amount { + volume { + value: 0.16507633 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.48018652 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "40" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "9.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile.Acetic Acid" + } + amount { + volume { + value: 0.19411388 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.98855 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "40" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "40" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "15.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile.Acetic Acid" + } + amount { + volume { + value: 0.35169166 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.007349 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "40" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "16.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 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Acid" + } + amount { + volume { + value: 0.39015335 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "40" + } + identifiers { + 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "40" + } + 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"Acetonitrile.Acetic Acid" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "41" + } + 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"Acetonitrile.Acetic Acid" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 2.0240173 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 5.057648 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "41" + } + identifiers { + 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "42" + } + 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"Acetonitrile.Acetic Acid" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.004683 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "42" + } + 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"Acetonitrile.Acetic Acid" + } + amount { + volume { + value: 0.48362967 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.998453 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.993669 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "42" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "42" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "8.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile.Acetic Acid" + } + amount { + volume { + value: 0.32950225 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "42" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "9.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile.Acetic Acid" + } + amount { + volume { + value: 0.28982714 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "42" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "42" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "15.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile.Acetic Acid" + } + amount { + volume { + value: 0.1327467 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.009465 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "42" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "16.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Acetonitrile.Acetic Acid" + } + amount { + volume { + value: 0.094447576 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.013584 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "42" + } + 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 14.481269 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "5" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "42" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 14.699383 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "43" + } + 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NAME + value: "Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 3.9679823 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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-7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 90.72533 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "43" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "2.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 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"Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 7.001613 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.7958044 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "43" + } + identifiers { + 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "44" + } + identifiers { + 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"Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.0024710582 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "44" + } + identifiers { + 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"Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.041150037 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.995207 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "44" + } + identifiers { + 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.991426 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.6528337 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "44" + } + identifiers { + 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"Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.19592173 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.43944204 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "44" + } + identifiers { + 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"Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.2355963 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988553 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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-7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 93.2368 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "44" + } + identifiers { + 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.989431 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 94.556526 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "44" + } + identifiers { + 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 96.57374 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "44" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "16.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.012294 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 97.60641 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "44" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "17.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 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Ether [Ether]" + } + amount { + volume { + value: 0.43042263 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.01543 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 98.65359 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "44" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "18.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 99.104866 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "44" + } + identifiers { + 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 98.80676 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "45" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "2.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 2.1622498 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 99.546646 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "45" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "3.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 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"Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 5.1958804 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 99.10284 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "45" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 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Ether [Ether]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 8.229548 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 100.00001 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "45" + } + identifiers { + 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 98.78145 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "46" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "2.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 98.52849 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "46" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "3.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 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Ether [Ether]" + } + amount { + volume { + value: 0.44320893 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.993488 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 96.70623 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 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CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 95.82361 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "46" + } + identifiers { + 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"Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.28801927 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "46" + } + identifiers { + 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"Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.24834798 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.98872 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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-7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 91.832825 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "46" + } + identifiers { + 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"Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.20869336 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.99023 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.45880046 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "46" + } + identifiers { + 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "46" + } + identifiers { + 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"Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.09250946 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "46" + } + identifiers { + 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"Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.05397313 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.016256 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "46" + } + identifiers { + 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.7116009 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "47" + } + identifiers { + 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"Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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"Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 178.60901 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "47" + } + identifiers { + 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "47" + } + 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NAME + value: "Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "47" + } + 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NAME + value: "Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 80.42584 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "48" + } + 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12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "O1C(C)CCC1" + } + identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CCOCC" + } + identifiers { + type: NAME + value: "Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 3.8235238 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 8.020526 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 65.73125 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "48" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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NAME + value: "Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 6.8571544 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 44.709114 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "48" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "48" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 24.800154 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "49" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "3.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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NAME + value: "Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.03930936 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 25.627861 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "49" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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NAME + value: "Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.07793897 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.99157 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 19.895506 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 25.880959 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "49" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "5.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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NAME + value: "Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.116516836 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.98928 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 19.541613 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 27.11916 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "49" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 32.23479 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "49" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "10.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "O1C(C)CCC1" + } + identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.2662928 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CCOCC" + } + identifiers { + type: NAME + value: "Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.2337072 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.98855 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 33.990406 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "49" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "11.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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NAME + value: "Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.27336985 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.989354 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 35.445126 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "49" + } + 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NAME + value: "Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.31301478 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 36.450962 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "49" + } + 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.012106 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 16.849674 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 44.45456 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "49" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "17.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "O1C(C)CCC1" + } + identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.071412615 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CCOCC" + } + identifiers { + type: NAME + value: "Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.42858738 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.015316 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 16.681175 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 46.516598 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "49" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "18.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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NAME + value: "Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.46715197 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.016967 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 45.89231 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "49" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 16.444363 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 46.538284 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "49" + } + 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 93.54198 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "50" + } + 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12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "O1C(C)CCC1" + } + identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CCOCC" + } + identifiers { + type: NAME + value: "Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 72.42252 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "50" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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NAME + value: "Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 8.085077 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 60.296116 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "50" + } + 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NAME + value: "Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 11.118862 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "50" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 12.005597 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 61.991062 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "51" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "3.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "O1C(C)CCC1" + } + identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.054951392 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CCOCC" + } + identifiers { + type: NAME + value: "Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.4450486 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.993677 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 12.778156 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 57.12126 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "51" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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NAME + value: "Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.40643996 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.990455 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 52.214363 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "51" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "5.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988796 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 15.51133 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 45.733864 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "51" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 33.034416 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "51" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "10.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "O1C(C)CCC1" + } + identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.24976325 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CCOCC" + } + identifiers { + type: NAME + value: "Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.25023675 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.9886875 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 18.29348 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 29.388218 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "51" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "11.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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NAME + value: "Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.21058127 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.990123 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 28.23576 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "51" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.013593 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 18.619024 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 22.911985 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "51" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "17.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "O1C(C)CCC1" + } + identifiers { + type: NAME + value: "2-Methyltetrahydrofuran [2-MeTHF]" + } + amount { + volume { + value: 0.44419062 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CCOCC" + } + identifiers { + type: NAME + value: "Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.055809364 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.016172 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 18.788454 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 21.663237 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "51" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "18.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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NAME + value: "Diethyl Ether [Ether]" + } + amount { + volume { + value: 0.01722389 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.01719 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 21.839794 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "51" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 18.292933 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 21.417398 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "6" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "51" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 2.001019 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 94.847046 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "52" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "2.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "OCC(F)(F)F" + } + identifiers { + type: NAME + value: "2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O.OCC(F)(F)F" + } + identifiers { + type: NAME + value: "Water.2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 3.933919 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.151998 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 94.87014 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "52" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "3.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 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"Water.2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 6.96755 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "52" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 10.0013275 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 8.040924 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "52" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 64.35312 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "53" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "3.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "OCC(F)(F)F" + } + identifiers { + type: NAME + value: "2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.45909992 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O.OCC(F)(F)F" + } + identifiers { + type: NAME + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.995236 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 13.263839 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 65.34573 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "53" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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value: "Water.2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.079343736 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.99146 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 67.4592 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "53" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.989219 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 10.074772 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 70.093285 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "53" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 65.125694 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "53" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "10.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "OCC(F)(F)F" + } + identifiers { + type: NAME + value: "2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.26466024 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O.OCC(F)(F)F" + } + identifiers { + type: NAME + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988552 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 14.981883 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 63.182194 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "53" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "11.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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value: "Water.2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.27500167 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.98942 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "53" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.991834 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 14.852704 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 61.648647 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "53" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.012269 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 56.274727 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "53" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "17.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "OCC(F)(F)F" + } + identifiers { + type: NAME + value: "2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.06982661 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O.OCC(F)(F)F" + } + identifiers { + type: NAME + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.015415 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 19.64809 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 54.908966 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "53" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "18.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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+ value: "Water.2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.4685563 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.016997 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 52.168728 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "53" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 19.856195 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 57.504593 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "53" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 2.1426325 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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-7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 99.45283 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "54" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "3.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "OCC(F)(F)F" + } + identifiers { + type: NAME + value: "2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O.OCC(F)(F)F" + } + identifiers { + type: NAME + value: "Water.2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 5.176263 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 2.9293385 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 92.65786 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "54" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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+ value: "Water.2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 8.2099285 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 78.19622 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "54" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 11.243706 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 14.70172 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 63.519825 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "54" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.998237 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 55.70222 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "55" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "3.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "OCC(F)(F)F" + } + identifiers { + type: NAME + value: "2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.056357287 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O.OCC(F)(F)F" + } + identifiers { + type: NAME 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.993532 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 16.815468 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 58.40353 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "55" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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value: "Water.2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.40503594 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.990367 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 59.25781 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "55" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988762 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 14.423695 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 60.46145 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "55" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 66.783806 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "55" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "10.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "OCC(F)(F)F" + } + identifiers { + type: NAME + value: "2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.25139552 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O.OCC(F)(F)F" + } + identifiers { + type: NAME + value: "Water.2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.24860448 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988715 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 12.944201 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 69.96683 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "55" + } + 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value: "Water.2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.20894973 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.990215 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 69.51141 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "55" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.993275 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 12.480912 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 66.31886 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "55" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.013714 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 67.956726 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "55" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "17.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "OCC(F)(F)F" + } + identifiers { + type: NAME + value: "2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.4457775 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O.OCC(F)(F)F" + } + identifiers { + type: NAME + value: "Water.2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.054222498 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.016245 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 11.202337 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 63.930264 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "55" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "18.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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value: "Water.2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.0156349 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017199 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "55" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 7.8589787 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 62.460278 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "55" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 60.685127 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "56" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "3.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Temperature Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "OCC(F)(F)F" + } + identifiers { + type: NAME + value: "2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O.OCC(F)(F)F" + } + identifiers { + type: NAME 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 178.59383 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 10.505902 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 46.204144 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "56" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Temperature Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 184.18465 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "56" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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-7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "56" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "10.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Temperature Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "OCC(F)(F)F" + } + identifiers { + type: NAME + value: "2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O.OCC(F)(F)F" + } + identifiers { + type: NAME + value: 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 9.11045e-08 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 4.189724e-08 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "56" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "11.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Temperature Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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+ value: "Water.2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "56" + } + identifiers { + 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type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "56" + 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 3.7894604 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 4.700735 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "57" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "OCC(F)(F)F" + } + identifiers { + type: NAME + value: "2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O.OCC(F)(F)F" + } + identifiers { + type: NAME + value: "Water.2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 6.823091 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 4.2801948 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "57" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "5.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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+ value: "Water.2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 9.871308 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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-7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "57" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "6.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 12.890526 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=CC=C1CC=C" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 2" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 19.778513 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "57" + } + identifiers { + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 3.3722196 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "58" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "OCC(F)(F)F" + } + identifiers { + type: NAME + value: "2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.42231068 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O.OCC(F)(F)F" + } + identifiers { + type: NAME + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.9915905 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 16.35742 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 5.8598666 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "58" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "5.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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value: "Water.2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.11608395 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.989297 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 15.284375 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 7.93083 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 9.111252 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "58" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "11.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "OCC(F)(F)F" + } + identifiers { + type: NAME + value: "2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.2268866 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O.OCC(F)(F)F" + } + identifiers { + type: NAME + value: "Water.2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.2731134 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.989344 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 23.054035 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 6.943593 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "58" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "12.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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value: "Water.2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.31275848 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.991697 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "58" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.995611 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 23.373322 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 4.81053 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "58" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.015288 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 1.5806575 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "58" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "18.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "OCC(F)(F)F" + } + identifiers { + type: NAME + value: "2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.033097595 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O.OCC(F)(F)F" + } + identifiers { + type: NAME 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.016961 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 25.41992 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.8279913 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "58" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "19.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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"Water.2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "58" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 27.9731 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "58" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 5.0318046 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "59" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "OCC(F)(F)F" + } + identifiers { + type: NAME + value: "2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O.OCC(F)(F)F" + } + identifiers { + type: NAME 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 8.051011 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 28.062311 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "59" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "5.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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+ value: "Water.2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 11.099245 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "59" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "6.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.118378 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 24.59788 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "59" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "7.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.993722 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "60" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "OCC(F)(F)F" + } + identifiers { + type: NAME + value: "2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.09331054 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O.OCC(F)(F)F" + } + identifiers { + type: NAME + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.990471 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 22.376753 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "60" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "5.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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value: "Water.2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.36813217 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988802 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "60" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 20.279037 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "60" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.98868 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "60" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "11.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "OCC(F)(F)F" + } + identifiers { + type: NAME + value: "2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.28897354 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O.OCC(F)(F)F" + } + identifiers { + type: NAME + value: "Water.2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.21102645 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.990098 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 12.086851 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "60" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "12.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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value: "Water.2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.17138846 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.993076 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "60" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "13.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.997614 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 11.56032 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "60" + } + 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.016151 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "60" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "18.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "OCC(F)(F)F" + } + identifiers { + type: NAME + value: "2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.48234257 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O.OCC(F)(F)F" + } + identifiers { + type: NAME + value: "Water.2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.017657436 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017188 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "7" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "60" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "19.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 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"Water.2,2,2-Trifluoroethanol" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 90.093704 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "61" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "3.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "CN(C)C(C)=O" + } + identifiers { + type: NAME + value: "DMA [N,N-Dimethylacetamide]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CCCCCCCCCCO" + } + identifiers { + type: NAME + value: "Decanol" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 7.008027 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 90.25318 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "61" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 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} + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 10.041806 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 90.88666 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "61" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "5.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 13.075457 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 90.600975 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "61" + } + identifiers { + 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 91.564705 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "62" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 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"Decanol" + } + amount { + volume { + value: 0.079858795 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.99142 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 90.84891 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "62" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "5.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 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} + amount { + volume { + value: 0.118434094 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.989206 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 90.49835 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "62" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "6.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "62" + } + identifiers { + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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-7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 89.90026 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "62" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "11.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 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"Decanol" + } + amount { + volume { + value: 0.27534193 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.989434 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 91.52447 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "62" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "12.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 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"Decanol" + } + amount { + volume { + value: 0.314986 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.991877 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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-7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 92.00497 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "62" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "13.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 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"Decanol" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.995878 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 89.42443 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "62" + } + identifiers { + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 84.14198 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "62" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "18.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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NAME + value: "Decanol" + } + amount { + volume { + value: 0.46907124 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017008 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.8577916 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 91.666756 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "62" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "19.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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value: "Decanol" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 87.37932 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 92.30037 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "62" + } + 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 83.56479 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "63" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 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} + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 8.235963 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 90.400375 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "63" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "5.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 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"Decanol" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 11.269737 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 91.72411 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "64" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "1.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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NAME + value: "Decanol" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 2.001019 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 90.95776 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "64" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "2.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 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-7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 90.39494 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "64" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "6.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "CN(C)C(C)=O" + } + identifiers { + type: NAME + value: "DMA [N,N-Dimethylacetamide]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CCCCCCCCCCO" + } + identifiers { + type: NAME + value: "Decanol" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 91.09412 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "64" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "7.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 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} + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 90.80163 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 89.97194 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "65" + } + 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NAME + value: "Decanol" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 189.17639 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 81.396805 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "65" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "6.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Temperature Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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NAME + value: "Decanol" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 198.29486 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "65" + } + 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 6.23334 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "65" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "12.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Temperature Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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NAME + value: "Decanol" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 6.4894037 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "65" + } + 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NAME + value: "Decanol" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "66" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 9.204754 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "66" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "6.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "CN(C)C(C)=O" + } + identifiers { + type: NAME + value: "DMA [N,N-Dimethylacetamide]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CCCCCCCCCCO" + } + identifiers { + type: NAME + value: "Decanol" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.123087 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 21.091434 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 6.6556973 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "66" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "7.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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NAME + value: "Decanol" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.010214 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 6.647432 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "67" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.004756 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 6.8499627 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "67" + } + 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 6.69648 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "67" + } + 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-8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "CN(C)C(C)=O" + } + identifiers { + type: NAME + value: "DMA [N,N-Dimethylacetamide]" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CCCCCCCCCCO" + } + identifiers { + type: NAME + value: "Decanol" + } + amount { + volume { + value: 0.16507633 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 33.93602 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 5.935101 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "67" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "7.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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NAME + value: "Decanol" + } + amount { + volume { + value: 0.16507633 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 6.1433907 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "67" + } + 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NAME + value: "Decanol" + } + amount { + volume { + value: 0.1700324 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 6.3241887 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "67" + } + 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "67" + } + 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NAME + value: "Decanol" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.9976225 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 34.768158 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 4.0060544 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "67" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "14.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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NAME + value: "Decanol" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.003697 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "67" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.009407 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "67" + } + 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "67" + } + 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value: "Decanol" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "68" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 9.433005 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "68" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "6.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "CN(C)C(C)=O" + } + identifiers { + type: NAME + value: "DMA [N,N-Dimethylacetamide]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CCCCCCCCCCO" + } + identifiers { + type: NAME + value: "Decanol" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 12.31741 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 38.419003 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "68" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "7.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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NAME + value: "Decanol" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.012721 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "68" + } + 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.008193 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "69" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "69" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "5.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "CN(C)C(C)=O" + } + identifiers { + type: NAME + value: "DMA [N,N-Dimethylacetamide]" + } + amount { + volume { + value: 0.14751948 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CCCCCCCCCCO" + } + identifiers { + type: NAME + value: "Decanol" + } + amount { + volume { + value: 0.35248053 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.98857 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 34.360054 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 0.0 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "69" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "6.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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NAME + value: "Decanol" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 5.289206 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "69" + } + 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NAME + value: "Decanol" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 33.428722 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 3.6423755 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "69" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.991119 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 5.522212 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "69" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "12.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "CN(C)C(C)=O" + } + identifiers { + type: NAME + value: "DMA [N,N-Dimethylacetamide]" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CCCCCCCCCCO" + } + identifiers { + type: NAME + value: "Decanol" + } + amount { + volume { + value: 0.16507633 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.994732 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 30.697922 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 5.628469 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "69" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "13.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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NAME + value: "Decanol" + } + amount { + volume { + value: 0.16507633 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.999904 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 3.96345 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "69" + } + 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NAME + value: "Decanol" + } + amount { + volume { + value: 0.15607923 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.006196 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 29.35967 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 5.6284466 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "69" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 6.6701164 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "69" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "19.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 6.7691536 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "8" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "69" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "20.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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value: "Decanol" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "70" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 10.017508 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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-7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 90.17245 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "70" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "5.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "OCC" + } + identifiers { + type: NAME + value: "Ethanol" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "C1CCOC1" + } + identifiers { + type: NAME + value: "THF [Tetrahydrofuran]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 13.05116 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.50133264 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 89.113174 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "70" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "6.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.011769 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 88.96795 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "71" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.006864 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.5580721 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 88.56887 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "71" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 87.94886 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "71" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "6.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.15664944 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 1.3537741 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 87.52466 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "71" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "7.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.16507633 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 87.64845 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "71" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "8.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.16507633 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 1.3880808 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 87.402534 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "71" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.991851 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.4591517 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 85.664734 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "71" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "13.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.995839 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.56132334 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 85.629326 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "71" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "14.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.001419 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 85.40783 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "71" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "15.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.35339954 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.007593 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.45176515 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 85.667725 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "71" + } + identifiers { + 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 92.46234 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "72" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "3.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 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volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 5.1779966 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 95.07492 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "72" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 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volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 8.2261095 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "72" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "5.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 11.24544 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 90.86054 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.998208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.23183082 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 85.67993 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "73" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "3.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "OCC" + } + identifiers { + type: NAME + value: "Ethanol" + } + amount { + volume { + value: 0.056563325 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "C1CCOC1" + } + identifiers { + type: NAME + value: "THF [Tetrahydrofuran]" + } + amount { + volume { + value: 0.44343668 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.993511 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=CC=C1CC=C" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 2" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 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datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 83.357414 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "73" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 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{ + volume { + value: 0.40464646 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.990343 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "73" + } + identifiers { + 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{ + volume { + value: 0.36627537 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988761 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "73" + } + identifiers { + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 88.17089 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "73" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "10.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.24839294 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.98872 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.61760575 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 94.00786 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "73" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "11.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.20892708 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.990216 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 91.15621 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "73" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "12.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.16929002 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.993278 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=CC=C1CC=C" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 2" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.1635676 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.55329835 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 96.66126 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "73" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "13.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.013747 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.6975332 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 106.03671 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "73" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "17.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.054200463 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.016246 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 108.32543 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "73" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "18.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 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{ + volume { + value: 0.01542896 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.0171995 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 97.24839 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "74" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "1.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 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volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 100.00001 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "74" + } + identifiers { + 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 81.74561 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "74" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "6.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "OCC" + } + identifiers { + type: NAME + value: "Ethanol" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "C1CCOC1" + } + identifiers { + type: NAME + value: "THF [Tetrahydrofuran]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 13.071777 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.4197895 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 80.674286 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "74" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "7.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 175.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 80.876564 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 80.76145 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "74" + } + 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 81.974495 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "75" + } + 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 180.65361 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 2.0587926 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 75.2834 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "75" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "5.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Temperature Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 186.96484 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 36.860653 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "75" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 5.157827 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "75" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "11.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Temperature Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 4.954248 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "75" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "12.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Temperature Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "75" + } + 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 5.11656 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "76" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 11.034118 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "76" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "5.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "OCC" + } + identifiers { + type: NAME + value: "Ethanol" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "C1CCOC1" + } + identifiers { + type: NAME + value: "THF [Tetrahydrofuran]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 11.309566 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 32.540695 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 5.139076 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "76" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "6.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.343128 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 4.9850206 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "76" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "7.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.009871 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 33.83612 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 4.90435 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "77" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.990305 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 37.493824 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 8.596843 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "77" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "5.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.13453905 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988744 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=CC=C1CC=C" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 2" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 33.777412 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 37.1833 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 9.194935 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "77" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "6.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.16507633 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 8.86458 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "77" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "7.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.16507633 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 9.505353 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "77" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.990265 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 31.502779 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 14.264569 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "77" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "12.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.33154765 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.993359 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 30.192919 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 14.209437 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "77" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "13.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.998013 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 14.232551 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "77" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "14.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.004164 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 28.349241 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 15.664942 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "77" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 21.556171 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "77" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "19.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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} + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 17.408821 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 21.001204 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "77" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "20.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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} + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 45.118977 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "78" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "5.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "OCC" + } + identifiers { + type: NAME + value: "Ethanol" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "C1CCOC1" + } + identifiers { + type: NAME + value: "THF [Tetrahydrofuran]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 9.503774 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 19.55245 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 29.685944 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "78" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "6.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 12.537461 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 20.094847 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "78" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "7.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.012445 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 16.30626 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 20.093584 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "78" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.991976 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 16.304604 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "79" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.3884034 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.989485 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 30.055403 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 14.895531 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "79" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "5.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.34987053 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988557 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 14.914708 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "79" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "6.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.33492365 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.988549 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 29.525581 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 15.172411 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "79" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.989164 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 10.249585 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "79" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "11.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.1920435 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.991329 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 38.724533 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 10.574894 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "79" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "12.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.16507633 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 14.995054 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 15.818915 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "79" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "13.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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[Tetrahydrofuran]" + } + amount { + volume { + value: 0.16507633 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.0003395 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 41.102253 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 11.939954 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "79" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.016843 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 7.8205013 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "79" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "18.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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} + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 225.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 40.175827 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 11.738352 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "79" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "19.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Solvent Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 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} + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "9" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "79" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 79.19483 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "10" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "80" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "[C@H]12CCC([C@H](OC1)O2)=O" + } + identifiers { + type: NAME + value: "Dihydrolevoglucosenone (Cyrene)" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O=C(OCC)C" + } + identifiers { + type: NAME + value: "Ethyl Acetate" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 10.038219 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 12.998896 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 68.66671 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "10" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "80" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "5.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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identifiers { + type: NAME + value: "Ethyl Acetate" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 13.07185 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 59.01154 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "10" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "80" + } + 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "10" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "80" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 56.533234 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "10" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "80" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "11.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "[C@H]12CCC([C@H](OC1)O2)=O" + } + identifiers { + type: NAME + value: "Dihydrolevoglucosenone (Cyrene)" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O=C(OCC)C" + } + identifiers { + type: NAME + value: "Ethyl Acetate" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 15.594571 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 56.65329 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "10" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "80" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "12.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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identifiers { + type: NAME + value: "Ethyl Acetate" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "10" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "80" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 57.18826 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "10" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "80" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "18.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "[C@H]12CCC([C@H](OC1)O2)=O" + } + identifiers { + type: NAME + value: "Dihydrolevoglucosenone (Cyrene)" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O=C(OCC)C" + } + identifiers { + type: NAME + value: "Ethyl Acetate" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 18.27005 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 58.760796 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "10" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "81" + } + 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identifiers { + type: NAME + value: "Ethyl Acetate" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 2.2085633 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 5.2421937 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 81.35826 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "10" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "81" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 67.96282 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "10" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "81" + } + 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12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "[C@H]12CCC([C@H](OC1)O2)=O" + } + identifiers { + type: NAME + value: "Dihydrolevoglucosenone (Cyrene)" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O=C(OCC)C" + } + identifiers { + type: NAME + value: "Ethyl Acetate" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 4.481427 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 67.86804 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "10" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "81" + } + 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identifiers { + type: NAME + value: "Ethyl Acetate" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 65.91009 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "10" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "81" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "14.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "[C@H]12CCC([C@H](OC1)O2)=O" + } + identifiers { + type: NAME + value: "Dihydrolevoglucosenone (Cyrene)" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O=C(OCC)C" + } + identifiers { + type: NAME + value: "Ethyl Acetate" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 4.6078787 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 65.971756 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "10" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "81" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "15.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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identifiers { + type: NAME + value: "Ethyl Acetate" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "10" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "81" + } + 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "10" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "81" + } + 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 3.975581 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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-7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 95.73855 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "11" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "82" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "3.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "CC(C)(C)OC" + } + identifiers { + type: NAME + value: "MTBE [tert-Butylmethylether]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CCC(=O)C" + } + identifiers { + type: NAME + value: "Butanone [MEK]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 6.9947658 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 92.51782 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "11" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "82" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 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"Butanone [MEK]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 10.042842 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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-7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 89.34096 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "11" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "82" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "5.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 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"Butanone [MEK]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 13.076472 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=CC=C1CC=C" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 2" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 7.8884816 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 2.0260067 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 86.06738 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "11" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "82" + } + 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 85.03058 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "11" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "82" + } + 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12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "CC(C)(C)OC" + } + identifiers { + type: NAME + value: "MTBE [tert-Butylmethylether]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CCC(=O)C" + } + identifiers { + type: NAME + value: "Butanone [MEK]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 85.45906 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "11" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "82" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "11.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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NAME + value: "Butanone [MEK]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 87.3067 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "11" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "82" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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" + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 6.0988326 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 83.30166 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "11" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "82" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 83.30305 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "11" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "83" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "1.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "CC(C)(C)OC" + } + identifiers { + type: NAME + value: "MTBE [tert-Butylmethylether]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CCC(=O)C" + } + identifiers { + type: NAME + value: "Butanone [MEK]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 2.19874 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 75.54297 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "11" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "83" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "2.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 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[MEK]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 5.2468166 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 71.72057 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "11" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "83" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "3.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "CC(C)(C)OC" + } + identifiers { + type: NAME + value: "MTBE [tert-Butylmethylether]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CCC(=O)C" + } + identifiers { + type: NAME + value: "Butanone [MEK]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 8.280447 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 2.2255156 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 66.508064 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "11" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "83" + } + 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 67.620125 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "11" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "83" + } + 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12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "CC(C)(C)OC" + } + identifiers { + type: NAME + value: "MTBE [tert-Butylmethylether]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CCC(=O)C" + } + identifiers { + type: 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 67.77003 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "11" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "83" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "9.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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NAME + value: "Butanone [MEK]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 67.98609 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "11" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "83" + } + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 4.6302943 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "11" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "83" + } + 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 89.27516 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "11" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "83" + } + 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12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "CC(C)(C)OC" + } + identifiers { + type: NAME + value: "MTBE [tert-Butylmethylether]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CCC(=O)C" + } + identifiers { + type: 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 71.29162 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "11" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "83" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "16.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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NAME + value: "Butanone [MEK]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 78.535286 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "11" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "83" + } + 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NAME + value: "Butanone [MEK]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 4.480465 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "11" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "83" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 78.17443 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "12" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "84" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "CC(C)(C)O" + } + identifiers { + type: NAME + value: "tert-Butanol [2-Methylpropan-2-ol]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "COC(=O)OC" + } + identifiers { + type: NAME + value: "Dimethyl Carbonate" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 9.993091 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 4.917637 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 70.63817 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "12" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "84" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "5.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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type: NAME + value: "Dimethyl Carbonate" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 13.026721 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 66.281944 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + 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12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "CC(C)(C)O" + } + identifiers { + type: NAME + value: "tert-Butanol [2-Methylpropan-2-ol]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "COC(=O)OC" + } + identifiers { + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 66.392876 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "12" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "84" + } + 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type: NAME + value: "Dimethyl Carbonate" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "CC(C)(C)O" + } + identifiers { + type: NAME + value: "tert-Butanol [2-Methylpropan-2-ol]" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "COC(=O)OC" + } + identifiers { + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "12" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "85" + } + 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type: NAME + value: "Dimethyl Carbonate" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 2.1634345 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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"Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "12" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "85" + } + identifiers { 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 97.49855 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "12" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "85" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 3.2086117 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 85.023834 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "12" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "85" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "7.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "CC(C)(C)O" + } + identifiers { + type: NAME + value: "tert-Butanol [2-Methylpropan-2-ol]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "COC(=O)OC" + } + identifiers { + type: NAME + value: "Dimethyl Carbonate" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 3.5758343 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 84.83925 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "12" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "85" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "8.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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type: NAME + value: "Dimethyl Carbonate" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 87.151085 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "12" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "85" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "14.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "CC(C)(C)O" + } + identifiers { + type: NAME + value: "tert-Butanol [2-Methylpropan-2-ol]" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "COC(=O)OC" + } + identifiers { + type: NAME + value: "Dimethyl Carbonate" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 3.8055696 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 84.78721 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "12" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "85" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "15.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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type: NAME + value: "Dimethyl Carbonate" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.38252223 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 79.64896 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "13" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "86" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "3.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 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Lactate" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 7.002783 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 1.1459508 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 75.915565 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "13" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "86" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "4.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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value: "Ethyl Lactate" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 10.036413 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 77.309906 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "13" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "86" + } + 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 70.16471 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "13" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "86" + } + 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value: "Ethyl Lactate" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 69.344536 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "13" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "86" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "11.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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value: "Ethyl Lactate" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "13" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "86" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 70.2123 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "13" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "86" + } + 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12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "O=C(OC)CC" + } + identifiers { + type: NAME + value: "Methyl Propionate" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CCOC(=O)C(C)O" + } + identifiers { + type: NAME + value: "Ethyl Lactate" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 70.09737 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "13" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "86" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "18.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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value: "Ethyl Lactate" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 70.11179 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + 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Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "13" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "87" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 59.408306 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "13" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "87" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "6.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "O=C(OC)CC" + } + identifiers { + type: NAME + value: "Methyl Propionate" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CCOC(=O)C(C)O" + } + identifiers { + type: NAME + value: "Ethyl Lactate" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 15.808296 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 59.81543 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "13" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "87" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "7.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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value: "Ethyl Lactate" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 61.025158 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "13" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "87" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "13.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: REACTANT + is_limiting: true + preparations { + } + } + components { + identifiers { + type: SMILES + value: "O=C(OC)CC" + } + identifiers { + type: NAME + value: "Methyl Propionate" + } + amount { + volume { + value: 0.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "CCOC(=O)C(C)O" + } + identifiers { + type: NAME + value: "Ethyl Lactate" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated 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16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 62.462166 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "13" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "87" + } + identifiers { + type: CUSTOM + details: "DATA POINT - index of the reactions within an individual ramp" + value: "14.0" + } + identifiers { + type: CUSTOM + details: "RAMP DESCRIPTION - Description of the ramp" + value: "Residence Time Ramp" + } + inputs { + key: "Combined flow" + value { + components { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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value: "Ethyl Lactate" + } + amount { + volume { + value: 0.5 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "ethyl benzene" + value: "CCc1ccccc1" + } + amount { + volume { + value: 0.1 + units: NANOLITER + } + volume_includes_solutes: false + } + reaction_role: INTERNAL_STANDARD + } + addition_device { + type: PISTON_PUMP + details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." + } + } + } + setup { + vessel { + type: TUBE + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + material { + type: METAL + details: "stainless steel" + } + volume { + value: 7.95 + units: MILLILITER + } + } + is_automated: true + environment { + type: CUSTOM + details: "Ventilated Cabinated" + } + } + conditions { + temperature { + control { + type: CUSTOM + details: "Agilent 6890 GC oven" + } + setpoint { + value: 200.0 + units: CELSIUS + } + } + pressure { + control { + type: PRESSURIZED + details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" + } + setpoint { + value: 55.0 + units: BAR + } + } + flow { + type: PLUG_FLOW_REACTOR + details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" + tubing { + type: STEEL + diameter { + value: 1.0 + units: MILLIMETER + } + } + } + conditions_are_dynamic: true + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + } + workups { + type: TEMPERATURE + details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." + temperature { + control { + type: DRY_ALUMINUM_PLATE + details: "customized cooling system made from an aluminum block and a Peltier assembly" + } + setpoint { + value: 5.0 + units: CELSIUS + } + } + is_automated: true + } + workups { + type: ALIQUOT + details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " + amount { + volume { + value: 500.0 + units: NANOLITER + } + } + is_automated: true + } + outcomes { + reaction_time { + value: 15.017208 + units: MINUTE + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 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details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." + value: "13" + } + identifiers { + type: CUSTOM + details: "RAMP NUM - Ramp number" + value: "87" + } + 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14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "Product 3" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + percentage { + value: 15.552541 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: MOLBLOCK + details: "Drawn with Ketcher" + value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" + } + identifiers { + type: SMILES + value: "C=CCOC1=C(OCC=C)C=CC=C1" + } + identifiers { + type: CUSTOM + details: "label from associated paper and datasets" + value: "SM" + } + measurements { + analysis_key: "HPLC" + type: YIELD + details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + percentage { + value: 61.570576 + } + } + reaction_role: REACTANT + } + analyses { + key: "HPLC" + value { + type: LC + details: "Agilent 1290 UPLC" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + experimenter { + name: "Sarah Boyall" + orcid: "0000-0001-5049-8335" + organization: "SOLVE Chemistry" + email: "sarah@solvechemistry.com" + } + city: "London" + experiment_start { + value: "2025-01-01T00:00:00" + } + publication_url: "https://arxiv.org/abs/2506.07619" + record_created { + time { + value: "2025-12-19T10:27:58" + } + person { + name: "Jose Pablo Folch" + orcid: "0000-0003-2586-4959" + organization: "SOLVE Chemistry" + email: "jose@solvechemistry.com" + } + } + } +} From 6cf5e9b45ebb41f82ce81014eaec09a96d051fef Mon Sep 17 00:00:00 2001 From: Ben Deadman Date: Fri, 13 Mar 2026 16:56:42 +0000 Subject: [PATCH 2/8] Updated dataset name and description, and corrected typo Added enhanced name and description to the dataset, and corrected the 'reactino' typo using search/replace. --- catechol_dataset_ord.pbtxt | 2458 ++++++++++++++++++------------------ 1 file changed, 1229 insertions(+), 1229 deletions(-) diff --git a/catechol_dataset_ord.pbtxt b/catechol_dataset_ord.pbtxt index 80d41a1..a018dec 100644 --- a/catechol_dataset_ord.pbtxt +++ b/catechol_dataset_ord.pbtxt @@ -1,5 +1,5 @@ -name: "catechol_dataset" -description: "Dataset for catechol reactions" +name: "Transient flow exploration of the effect of temperature, residence time and binary solvent ratios on a uni-molecular allyl substituted catechol reaction." +description: "1,227 datapoints were collected in a series of transient flow ramps involving temperature [175 - 225 C], residence time [2 - 15 minutes] and binary solvent ratios of 24 solvents. HPLC yields reported for starting material and 2 products of the uni-molecular rearrangement of o-Bis(allyloxy)benzene. Reactions performed by SOLVE Chemistry in London (solvechemistry.com) and published in https://doi.org/10.48550/arXiv.2506.07619." reactions { identifiers { type: CUSTOM @@ -155,7 +155,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -460,7 +460,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -765,7 +765,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -1070,7 +1070,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -1375,7 +1375,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -1680,7 +1680,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -1985,7 +1985,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -2290,7 +2290,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -2595,7 +2595,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -2900,7 +2900,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -3205,7 +3205,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -3510,7 +3510,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -3815,7 +3815,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -4120,7 +4120,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -4425,7 +4425,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -4730,7 +4730,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -5035,7 +5035,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -5340,7 +5340,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -5645,7 +5645,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -5950,7 +5950,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -6255,7 +6255,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -6560,7 +6560,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -6865,7 +6865,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -7170,7 +7170,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -7475,7 +7475,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -7780,7 +7780,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -8085,7 +8085,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -8390,7 +8390,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -8695,7 +8695,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -9000,7 +9000,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -9305,7 +9305,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -9610,7 +9610,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -9915,7 +9915,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -10220,7 +10220,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -10525,7 +10525,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -10830,7 +10830,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -11135,7 +11135,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -11440,7 +11440,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -11745,7 +11745,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -12050,7 +12050,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -12355,7 +12355,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -12660,7 +12660,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -12965,7 +12965,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -13270,7 +13270,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -13575,7 +13575,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -13880,7 +13880,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -14185,7 +14185,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -14490,7 +14490,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -14795,7 +14795,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -15100,7 +15100,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -15405,7 +15405,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -15710,7 +15710,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -16015,7 +16015,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -16320,7 +16320,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -16625,7 +16625,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -16930,7 +16930,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -17235,7 +17235,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -17540,7 +17540,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -17845,7 +17845,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -18150,7 +18150,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -18455,7 +18455,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -18760,7 +18760,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -19065,7 +19065,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -19370,7 +19370,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -19675,7 +19675,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -19980,7 +19980,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -20285,7 +20285,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -20590,7 +20590,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -20895,7 +20895,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -21200,7 +21200,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -21505,7 +21505,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -21810,7 +21810,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -22115,7 +22115,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -22420,7 +22420,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -22725,7 +22725,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -23030,7 +23030,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -23335,7 +23335,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -23640,7 +23640,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -23945,7 +23945,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -24250,7 +24250,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -24555,7 +24555,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -24860,7 +24860,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -25165,7 +25165,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -25470,7 +25470,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -25775,7 +25775,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -26080,7 +26080,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -26385,7 +26385,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -26690,7 +26690,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -26995,7 +26995,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -27300,7 +27300,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -27605,7 +27605,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -27910,7 +27910,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -28215,7 +28215,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -28520,7 +28520,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -28825,7 +28825,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -29130,7 +29130,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -29435,7 +29435,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -29740,7 +29740,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -30045,7 +30045,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -30350,7 +30350,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -30655,7 +30655,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -30960,7 +30960,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -31265,7 +31265,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -31570,7 +31570,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -31875,7 +31875,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -32180,7 +32180,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -32485,7 +32485,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -32790,7 +32790,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -33095,7 +33095,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -33400,7 +33400,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -33705,7 +33705,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -34010,7 +34010,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -34315,7 +34315,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -34620,7 +34620,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -34925,7 +34925,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -35230,7 +35230,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -35535,7 +35535,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -35840,7 +35840,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -36145,7 +36145,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -36450,7 +36450,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -36755,7 +36755,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -37060,7 +37060,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -37365,7 +37365,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -37670,7 +37670,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -37975,7 +37975,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -38280,7 +38280,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -38585,7 +38585,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -38890,7 +38890,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -39195,7 +39195,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -39500,7 +39500,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -39805,7 +39805,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -40110,7 +40110,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -40415,7 +40415,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -40720,7 +40720,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -41025,7 +41025,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -41330,7 +41330,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -41635,7 +41635,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -41940,7 +41940,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -42245,7 +42245,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -42550,7 +42550,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -42855,7 +42855,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -43160,7 +43160,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -43465,7 +43465,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -43770,7 +43770,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -44075,7 +44075,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -44380,7 +44380,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -44685,7 +44685,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -44990,7 +44990,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -45295,7 +45295,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -45600,7 +45600,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -45905,7 +45905,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -46210,7 +46210,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -46515,7 +46515,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -46820,7 +46820,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -47125,7 +47125,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -47430,7 +47430,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -47735,7 +47735,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -48040,7 +48040,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -48345,7 +48345,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -48650,7 +48650,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -48955,7 +48955,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -49260,7 +49260,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -49565,7 +49565,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -49870,7 +49870,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -50175,7 +50175,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -50480,7 +50480,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -50785,7 +50785,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -51090,7 +51090,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -51395,7 +51395,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -51700,7 +51700,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -52005,7 +52005,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -52310,7 +52310,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -52615,7 +52615,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -52920,7 +52920,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -53225,7 +53225,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -53530,7 +53530,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -53835,7 +53835,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -54140,7 +54140,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -54445,7 +54445,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -54750,7 +54750,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -55055,7 +55055,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -55360,7 +55360,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -55665,7 +55665,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -55970,7 +55970,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -56275,7 +56275,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -56580,7 +56580,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -56885,7 +56885,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -57190,7 +57190,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -57495,7 +57495,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -57800,7 +57800,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -58105,7 +58105,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -58410,7 +58410,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -58715,7 +58715,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -59020,7 +59020,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -59325,7 +59325,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -59630,7 +59630,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -59935,7 +59935,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -60240,7 +60240,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -60545,7 +60545,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -60850,7 +60850,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -61155,7 +61155,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -61460,7 +61460,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -61765,7 +61765,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -62070,7 +62070,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -62375,7 +62375,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -62680,7 +62680,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -62985,7 +62985,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -63290,7 +63290,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -63595,7 +63595,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -63900,7 +63900,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -64205,7 +64205,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -64510,7 +64510,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -64815,7 +64815,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -65120,7 +65120,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -65425,7 +65425,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -65730,7 +65730,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -66035,7 +66035,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -66340,7 +66340,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -66645,7 +66645,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -66950,7 +66950,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -67255,7 +67255,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -67560,7 +67560,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -67865,7 +67865,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -68170,7 +68170,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -68475,7 +68475,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -68780,7 +68780,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -69085,7 +69085,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -69390,7 +69390,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -69695,7 +69695,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -70000,7 +70000,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -70305,7 +70305,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -70610,7 +70610,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -70915,7 +70915,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -71220,7 +71220,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -71525,7 +71525,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -71830,7 +71830,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -72135,7 +72135,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -72440,7 +72440,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -72745,7 +72745,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -73050,7 +73050,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -73355,7 +73355,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -73660,7 +73660,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -73965,7 +73965,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -74270,7 +74270,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -74575,7 +74575,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -74880,7 +74880,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -75185,7 +75185,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -75490,7 +75490,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -75795,7 +75795,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -76100,7 +76100,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -76405,7 +76405,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -76710,7 +76710,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -77015,7 +77015,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -77320,7 +77320,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -77625,7 +77625,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -77930,7 +77930,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -78235,7 +78235,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -78540,7 +78540,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -78845,7 +78845,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -79150,7 +79150,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -79455,7 +79455,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -79760,7 +79760,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -80065,7 +80065,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -80370,7 +80370,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -80675,7 +80675,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -80980,7 +80980,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -81285,7 +81285,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -81590,7 +81590,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -81895,7 +81895,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -82200,7 +82200,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -82505,7 +82505,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -82810,7 +82810,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -83115,7 +83115,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -83420,7 +83420,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -83725,7 +83725,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -84030,7 +84030,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -84335,7 +84335,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -84640,7 +84640,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -84945,7 +84945,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -85250,7 +85250,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -85555,7 +85555,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -85860,7 +85860,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -86165,7 +86165,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -86470,7 +86470,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -86775,7 +86775,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -87080,7 +87080,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -87385,7 +87385,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -87690,7 +87690,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -87995,7 +87995,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -88300,7 +88300,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -88605,7 +88605,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -88910,7 +88910,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -89215,7 +89215,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -89520,7 +89520,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -89825,7 +89825,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -90130,7 +90130,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -90435,7 +90435,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -90740,7 +90740,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -91045,7 +91045,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -91350,7 +91350,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -91655,7 +91655,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -91960,7 +91960,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -92265,7 +92265,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -92570,7 +92570,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -92875,7 +92875,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -93180,7 +93180,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -93485,7 +93485,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -93790,7 +93790,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -94095,7 +94095,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -94400,7 +94400,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -94705,7 +94705,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -95010,7 +95010,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -95315,7 +95315,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -95620,7 +95620,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -95925,7 +95925,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -96230,7 +96230,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -96535,7 +96535,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -96840,7 +96840,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -97145,7 +97145,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -97450,7 +97450,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -97755,7 +97755,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -98060,7 +98060,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -98365,7 +98365,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -98670,7 +98670,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -98975,7 +98975,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -99280,7 +99280,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -99585,7 +99585,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -99890,7 +99890,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -100195,7 +100195,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -100500,7 +100500,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -100805,7 +100805,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -101110,7 +101110,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -101415,7 +101415,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -101720,7 +101720,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -102025,7 +102025,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -102330,7 +102330,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -102635,7 +102635,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -102940,7 +102940,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -103245,7 +103245,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -103550,7 +103550,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -103855,7 +103855,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -104160,7 +104160,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -104465,7 +104465,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -104770,7 +104770,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -105075,7 +105075,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -105380,7 +105380,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -105685,7 +105685,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -105990,7 +105990,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -106295,7 +106295,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -106600,7 +106600,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -106905,7 +106905,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -107210,7 +107210,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -107515,7 +107515,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -107820,7 +107820,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -108125,7 +108125,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -108430,7 +108430,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -108735,7 +108735,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -109040,7 +109040,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -109345,7 +109345,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -109650,7 +109650,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -109955,7 +109955,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -110260,7 +110260,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -110565,7 +110565,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -110870,7 +110870,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -111175,7 +111175,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -111480,7 +111480,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -111785,7 +111785,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -112090,7 +112090,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -112395,7 +112395,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -112700,7 +112700,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -113005,7 +113005,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -113310,7 +113310,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -113615,7 +113615,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -113920,7 +113920,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -114225,7 +114225,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -114530,7 +114530,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -114835,7 +114835,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -115140,7 +115140,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -115445,7 +115445,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -115750,7 +115750,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -116055,7 +116055,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -116360,7 +116360,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -116665,7 +116665,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -116970,7 +116970,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -117275,7 +117275,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -117580,7 +117580,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -117885,7 +117885,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -118190,7 +118190,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -118495,7 +118495,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -118800,7 +118800,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -119105,7 +119105,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -119410,7 +119410,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -119715,7 +119715,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -120020,7 +120020,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -120325,7 +120325,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -120630,7 +120630,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -120935,7 +120935,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -121240,7 +121240,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -121545,7 +121545,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -121850,7 +121850,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -122155,7 +122155,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -122460,7 +122460,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -122765,7 +122765,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -123070,7 +123070,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -123375,7 +123375,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -123680,7 +123680,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -123985,7 +123985,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -124290,7 +124290,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -124595,7 +124595,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -124900,7 +124900,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -125205,7 +125205,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -125510,7 +125510,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -125815,7 +125815,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -126120,7 +126120,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -126425,7 +126425,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -126730,7 +126730,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -127035,7 +127035,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -127340,7 +127340,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -127645,7 +127645,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -127950,7 +127950,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -128255,7 +128255,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -128560,7 +128560,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -128865,7 +128865,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -129170,7 +129170,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -129475,7 +129475,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -129780,7 +129780,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -130085,7 +130085,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -130390,7 +130390,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -130695,7 +130695,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -131000,7 +131000,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -131305,7 +131305,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -131610,7 +131610,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -131915,7 +131915,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -132220,7 +132220,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -132525,7 +132525,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -132830,7 +132830,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -133135,7 +133135,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -133440,7 +133440,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -133745,7 +133745,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -134050,7 +134050,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -134355,7 +134355,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -134660,7 +134660,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -134965,7 +134965,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -135270,7 +135270,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -135575,7 +135575,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -135880,7 +135880,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -136185,7 +136185,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -136490,7 +136490,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -136795,7 +136795,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -137100,7 +137100,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -137405,7 +137405,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -137710,7 +137710,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -138015,7 +138015,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -138320,7 +138320,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -138625,7 +138625,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -138930,7 +138930,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -139235,7 +139235,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -139540,7 +139540,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -139845,7 +139845,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -140150,7 +140150,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -140455,7 +140455,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -140760,7 +140760,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -141065,7 +141065,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -141370,7 +141370,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -141675,7 +141675,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -141980,7 +141980,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -142285,7 +142285,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -142590,7 +142590,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -142895,7 +142895,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -143200,7 +143200,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -143505,7 +143505,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -143810,7 +143810,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -144115,7 +144115,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -144420,7 +144420,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -144725,7 +144725,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -145030,7 +145030,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -145335,7 +145335,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -145640,7 +145640,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -145945,7 +145945,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -146250,7 +146250,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -146555,7 +146555,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -146860,7 +146860,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -147165,7 +147165,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -147470,7 +147470,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -147775,7 +147775,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -148080,7 +148080,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -148385,7 +148385,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -148690,7 +148690,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -148995,7 +148995,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -149300,7 +149300,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -149605,7 +149605,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -149910,7 +149910,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -150215,7 +150215,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -150520,7 +150520,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -150825,7 +150825,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -151130,7 +151130,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -151435,7 +151435,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -151740,7 +151740,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -152045,7 +152045,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -152350,7 +152350,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -152655,7 +152655,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -152960,7 +152960,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -153265,7 +153265,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -153570,7 +153570,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -153875,7 +153875,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -154180,7 +154180,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -154485,7 +154485,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -154790,7 +154790,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -155095,7 +155095,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -155400,7 +155400,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -155705,7 +155705,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -156010,7 +156010,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -156315,7 +156315,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -156620,7 +156620,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -156925,7 +156925,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -157230,7 +157230,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -157535,7 +157535,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -157840,7 +157840,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -158145,7 +158145,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -158450,7 +158450,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -158755,7 +158755,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -159060,7 +159060,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -159365,7 +159365,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -159670,7 +159670,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -159975,7 +159975,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -160280,7 +160280,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -160585,7 +160585,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -160890,7 +160890,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -161195,7 +161195,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -161500,7 +161500,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -161805,7 +161805,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -162110,7 +162110,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -162415,7 +162415,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -162720,7 +162720,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -163025,7 +163025,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -163330,7 +163330,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -163635,7 +163635,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -163940,7 +163940,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -164245,7 +164245,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -164550,7 +164550,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -164855,7 +164855,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -165160,7 +165160,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -165465,7 +165465,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -165770,7 +165770,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -166075,7 +166075,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -166380,7 +166380,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -166685,7 +166685,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -166990,7 +166990,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -167295,7 +167295,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -167600,7 +167600,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -167905,7 +167905,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -168210,7 +168210,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -168515,7 +168515,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -168820,7 +168820,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -169125,7 +169125,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -169430,7 +169430,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -169735,7 +169735,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -170040,7 +170040,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -170345,7 +170345,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -170650,7 +170650,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -170955,7 +170955,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -171260,7 +171260,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -171565,7 +171565,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -171870,7 +171870,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -172175,7 +172175,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -172480,7 +172480,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -172785,7 +172785,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -173090,7 +173090,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -173395,7 +173395,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -173700,7 +173700,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -174005,7 +174005,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -174310,7 +174310,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -174615,7 +174615,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -174920,7 +174920,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -175225,7 +175225,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -175530,7 +175530,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -175835,7 +175835,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -176140,7 +176140,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -176445,7 +176445,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -176750,7 +176750,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -177055,7 +177055,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -177360,7 +177360,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -177665,7 +177665,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -177970,7 +177970,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -178275,7 +178275,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -178580,7 +178580,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -178885,7 +178885,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -179190,7 +179190,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -179495,7 +179495,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -179800,7 +179800,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -180105,7 +180105,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -180410,7 +180410,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -180715,7 +180715,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -181020,7 +181020,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -181325,7 +181325,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -181630,7 +181630,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -181935,7 +181935,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -182240,7 +182240,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -182545,7 +182545,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -182850,7 +182850,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -183155,7 +183155,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -183460,7 +183460,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -183765,7 +183765,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -184070,7 +184070,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -184375,7 +184375,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -184680,7 +184680,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -184985,7 +184985,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -185290,7 +185290,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -185595,7 +185595,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -185900,7 +185900,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -186205,7 +186205,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -186510,7 +186510,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -186815,7 +186815,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -187120,7 +187120,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -187425,7 +187425,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -187730,7 +187730,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -188035,7 +188035,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -188340,7 +188340,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -188645,7 +188645,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -188950,7 +188950,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -189255,7 +189255,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -189560,7 +189560,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -189865,7 +189865,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -190170,7 +190170,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -190475,7 +190475,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -190780,7 +190780,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -191085,7 +191085,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -191390,7 +191390,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -191695,7 +191695,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -192000,7 +192000,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -192305,7 +192305,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -192610,7 +192610,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -192915,7 +192915,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -193220,7 +193220,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -193525,7 +193525,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -193830,7 +193830,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -194135,7 +194135,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -194440,7 +194440,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -194745,7 +194745,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -195050,7 +195050,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -195355,7 +195355,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -195660,7 +195660,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -195965,7 +195965,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -196270,7 +196270,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -196575,7 +196575,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -196880,7 +196880,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -197185,7 +197185,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -197490,7 +197490,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -197795,7 +197795,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -198100,7 +198100,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -198405,7 +198405,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -198710,7 +198710,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -199015,7 +199015,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -199320,7 +199320,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -199625,7 +199625,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -199930,7 +199930,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -200235,7 +200235,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -200540,7 +200540,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -200845,7 +200845,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -201150,7 +201150,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -201455,7 +201455,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -201760,7 +201760,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -202065,7 +202065,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -202370,7 +202370,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -202675,7 +202675,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -202980,7 +202980,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -203285,7 +203285,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -203590,7 +203590,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -203895,7 +203895,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -204200,7 +204200,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -204505,7 +204505,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -204810,7 +204810,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -205115,7 +205115,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -205420,7 +205420,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -205725,7 +205725,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -206030,7 +206030,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -206335,7 +206335,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -206640,7 +206640,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -206945,7 +206945,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -207250,7 +207250,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -207555,7 +207555,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -207860,7 +207860,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -208165,7 +208165,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -208470,7 +208470,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -208775,7 +208775,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -209080,7 +209080,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -209385,7 +209385,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -209690,7 +209690,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -209995,7 +209995,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -210300,7 +210300,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -210605,7 +210605,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -210910,7 +210910,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -211215,7 +211215,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -211520,7 +211520,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -211825,7 +211825,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -212130,7 +212130,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -212435,7 +212435,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -212740,7 +212740,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -213045,7 +213045,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -213350,7 +213350,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -213655,7 +213655,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -213960,7 +213960,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -214265,7 +214265,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -214570,7 +214570,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -214875,7 +214875,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -215180,7 +215180,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -215485,7 +215485,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -215790,7 +215790,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -216095,7 +216095,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -216400,7 +216400,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -216705,7 +216705,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -217010,7 +217010,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -217315,7 +217315,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -217620,7 +217620,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -217925,7 +217925,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -218230,7 +218230,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -218535,7 +218535,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -218840,7 +218840,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -219145,7 +219145,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -219450,7 +219450,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -219755,7 +219755,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -220060,7 +220060,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -220365,7 +220365,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -220670,7 +220670,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -220975,7 +220975,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -221280,7 +221280,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -221585,7 +221585,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -221890,7 +221890,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -222195,7 +222195,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -222500,7 +222500,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -222805,7 +222805,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -223110,7 +223110,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -223415,7 +223415,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -223720,7 +223720,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -224025,7 +224025,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -224330,7 +224330,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -224635,7 +224635,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -224940,7 +224940,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -225245,7 +225245,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -225550,7 +225550,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -225855,7 +225855,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -226160,7 +226160,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -226465,7 +226465,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -226770,7 +226770,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -227075,7 +227075,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -227380,7 +227380,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -227685,7 +227685,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -227990,7 +227990,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -228295,7 +228295,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -228600,7 +228600,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -228905,7 +228905,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -229210,7 +229210,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -229515,7 +229515,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -229820,7 +229820,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -230125,7 +230125,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -230430,7 +230430,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -230735,7 +230735,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -231040,7 +231040,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -231345,7 +231345,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -231650,7 +231650,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -231955,7 +231955,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -232260,7 +232260,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -232565,7 +232565,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -232870,7 +232870,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -233175,7 +233175,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -233480,7 +233480,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -233785,7 +233785,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -234090,7 +234090,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -234395,7 +234395,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -234700,7 +234700,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -235005,7 +235005,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -235310,7 +235310,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -235615,7 +235615,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -235920,7 +235920,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -236225,7 +236225,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -236530,7 +236530,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -236835,7 +236835,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -237140,7 +237140,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -237445,7 +237445,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -237750,7 +237750,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -238055,7 +238055,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -238360,7 +238360,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -238665,7 +238665,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -238970,7 +238970,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -239275,7 +239275,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -239580,7 +239580,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -239885,7 +239885,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -240190,7 +240190,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -240495,7 +240495,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -240800,7 +240800,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -241105,7 +241105,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -241410,7 +241410,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -241715,7 +241715,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -242020,7 +242020,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -242325,7 +242325,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -242630,7 +242630,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -242935,7 +242935,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -243240,7 +243240,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -243545,7 +243545,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -243850,7 +243850,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -244155,7 +244155,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -244460,7 +244460,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -244765,7 +244765,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -245070,7 +245070,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -245375,7 +245375,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -245680,7 +245680,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -245985,7 +245985,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -246290,7 +246290,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -246595,7 +246595,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -246900,7 +246900,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -247205,7 +247205,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -247510,7 +247510,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -247815,7 +247815,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -248120,7 +248120,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -248425,7 +248425,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -248730,7 +248730,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -249035,7 +249035,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -249340,7 +249340,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -249645,7 +249645,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -249950,7 +249950,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -250255,7 +250255,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -250560,7 +250560,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -250865,7 +250865,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -251170,7 +251170,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -251475,7 +251475,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -251780,7 +251780,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -252085,7 +252085,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -252390,7 +252390,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -252695,7 +252695,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -253000,7 +253000,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -253305,7 +253305,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -253610,7 +253610,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -253915,7 +253915,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -254220,7 +254220,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -254525,7 +254525,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -254830,7 +254830,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -255135,7 +255135,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -255440,7 +255440,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -255745,7 +255745,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -256050,7 +256050,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -256355,7 +256355,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -256660,7 +256660,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -256965,7 +256965,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -257270,7 +257270,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -257575,7 +257575,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -257880,7 +257880,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -258185,7 +258185,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -258490,7 +258490,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -258795,7 +258795,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -259100,7 +259100,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -259405,7 +259405,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -259710,7 +259710,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -260015,7 +260015,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -260320,7 +260320,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -260625,7 +260625,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -260930,7 +260930,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -261235,7 +261235,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -261540,7 +261540,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -261845,7 +261845,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -262150,7 +262150,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -262455,7 +262455,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -262760,7 +262760,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -263065,7 +263065,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -263370,7 +263370,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -263675,7 +263675,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -263980,7 +263980,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -264285,7 +264285,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -264590,7 +264590,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -264895,7 +264895,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -265200,7 +265200,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -265505,7 +265505,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -265810,7 +265810,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -266115,7 +266115,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -266420,7 +266420,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -266725,7 +266725,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -267030,7 +267030,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -267335,7 +267335,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -267640,7 +267640,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -267945,7 +267945,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -268250,7 +268250,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -268555,7 +268555,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -268860,7 +268860,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -269165,7 +269165,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -269470,7 +269470,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -269775,7 +269775,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -270080,7 +270080,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -270385,7 +270385,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -270690,7 +270690,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -270995,7 +270995,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -271300,7 +271300,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -271605,7 +271605,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -271910,7 +271910,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -272215,7 +272215,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -272520,7 +272520,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -272825,7 +272825,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -273130,7 +273130,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -273435,7 +273435,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -273740,7 +273740,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -274045,7 +274045,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -274350,7 +274350,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -274655,7 +274655,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -274960,7 +274960,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -275265,7 +275265,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -275570,7 +275570,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -275875,7 +275875,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -276180,7 +276180,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -276485,7 +276485,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -276790,7 +276790,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -277095,7 +277095,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -277400,7 +277400,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -277705,7 +277705,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -278010,7 +278010,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -278315,7 +278315,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -278620,7 +278620,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -278925,7 +278925,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -279230,7 +279230,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -279535,7 +279535,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -279840,7 +279840,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -280145,7 +280145,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -280450,7 +280450,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -280755,7 +280755,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -281060,7 +281060,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -281365,7 +281365,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -281670,7 +281670,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -281975,7 +281975,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -282280,7 +282280,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -282585,7 +282585,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -282890,7 +282890,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -283195,7 +283195,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -283500,7 +283500,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -283805,7 +283805,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -284110,7 +284110,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -284415,7 +284415,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -284720,7 +284720,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -285025,7 +285025,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -285330,7 +285330,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -285635,7 +285635,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -285940,7 +285940,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -286245,7 +286245,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -286550,7 +286550,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -286855,7 +286855,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -287160,7 +287160,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -287465,7 +287465,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -287770,7 +287770,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -288075,7 +288075,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -288380,7 +288380,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -288685,7 +288685,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -288990,7 +288990,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -289295,7 +289295,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -289600,7 +289600,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -289905,7 +289905,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -290210,7 +290210,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -290515,7 +290515,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -290820,7 +290820,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -291125,7 +291125,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -291430,7 +291430,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -291735,7 +291735,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -292040,7 +292040,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -292345,7 +292345,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -292650,7 +292650,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -292955,7 +292955,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -293260,7 +293260,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -293565,7 +293565,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -293870,7 +293870,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -294175,7 +294175,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -294480,7 +294480,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -294785,7 +294785,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -295090,7 +295090,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -295395,7 +295395,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -295700,7 +295700,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -296005,7 +296005,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -296310,7 +296310,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -296615,7 +296615,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -296920,7 +296920,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -297225,7 +297225,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -297530,7 +297530,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -297835,7 +297835,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -298140,7 +298140,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -298445,7 +298445,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -298750,7 +298750,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -299055,7 +299055,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -299360,7 +299360,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -299665,7 +299665,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -299970,7 +299970,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -300275,7 +300275,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -300580,7 +300580,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -300885,7 +300885,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -301190,7 +301190,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -301495,7 +301495,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -301800,7 +301800,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -302105,7 +302105,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -302410,7 +302410,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -302715,7 +302715,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -303020,7 +303020,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -303325,7 +303325,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -303630,7 +303630,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -303935,7 +303935,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -304240,7 +304240,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -304545,7 +304545,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -304850,7 +304850,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -305155,7 +305155,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -305460,7 +305460,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -305765,7 +305765,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -306070,7 +306070,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -306375,7 +306375,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -306680,7 +306680,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -306985,7 +306985,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -307290,7 +307290,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -307595,7 +307595,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -307900,7 +307900,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -308205,7 +308205,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -308510,7 +308510,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -308815,7 +308815,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -309120,7 +309120,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -309425,7 +309425,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -309730,7 +309730,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -310035,7 +310035,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -310340,7 +310340,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -310645,7 +310645,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -310950,7 +310950,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -311255,7 +311255,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -311560,7 +311560,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -311865,7 +311865,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -312170,7 +312170,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -312475,7 +312475,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -312780,7 +312780,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -313085,7 +313085,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -313390,7 +313390,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -313695,7 +313695,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -314000,7 +314000,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -314305,7 +314305,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -314610,7 +314610,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -314915,7 +314915,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -315220,7 +315220,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -315525,7 +315525,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -315830,7 +315830,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -316135,7 +316135,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -316440,7 +316440,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -316745,7 +316745,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -317050,7 +317050,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -317355,7 +317355,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -317660,7 +317660,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -317965,7 +317965,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -318270,7 +318270,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -318575,7 +318575,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -318880,7 +318880,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -319185,7 +319185,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -319490,7 +319490,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -319795,7 +319795,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -320100,7 +320100,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -320405,7 +320405,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -320710,7 +320710,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -321015,7 +321015,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -321320,7 +321320,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -321625,7 +321625,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -321930,7 +321930,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -322235,7 +322235,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -322540,7 +322540,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -322845,7 +322845,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -323150,7 +323150,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -323455,7 +323455,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -323760,7 +323760,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -324065,7 +324065,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -324370,7 +324370,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -324675,7 +324675,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -324980,7 +324980,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -325285,7 +325285,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -325590,7 +325590,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -325895,7 +325895,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -326200,7 +326200,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -326505,7 +326505,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -326810,7 +326810,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -327115,7 +327115,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -327420,7 +327420,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -327725,7 +327725,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -328030,7 +328030,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -328335,7 +328335,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -328640,7 +328640,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -328945,7 +328945,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -329250,7 +329250,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -329555,7 +329555,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -329860,7 +329860,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -330165,7 +330165,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -330470,7 +330470,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -330775,7 +330775,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -331080,7 +331080,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -331385,7 +331385,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -331690,7 +331690,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -331995,7 +331995,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -332300,7 +332300,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -332605,7 +332605,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -332910,7 +332910,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -333215,7 +333215,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -333520,7 +333520,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -333825,7 +333825,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -334130,7 +334130,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -334435,7 +334435,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -334740,7 +334740,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -335045,7 +335045,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -335350,7 +335350,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -335655,7 +335655,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -335960,7 +335960,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -336265,7 +336265,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -336570,7 +336570,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -336875,7 +336875,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -337180,7 +337180,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -337485,7 +337485,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -337790,7 +337790,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -338095,7 +338095,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -338400,7 +338400,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -338705,7 +338705,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -339010,7 +339010,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -339315,7 +339315,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -339620,7 +339620,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -339925,7 +339925,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -340230,7 +340230,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -340535,7 +340535,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -340840,7 +340840,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -341145,7 +341145,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -341450,7 +341450,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -341755,7 +341755,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -342060,7 +342060,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -342365,7 +342365,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -342670,7 +342670,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -342975,7 +342975,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -343280,7 +343280,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -343585,7 +343585,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -343890,7 +343890,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -344195,7 +344195,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -344500,7 +344500,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -344805,7 +344805,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -345110,7 +345110,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -345415,7 +345415,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -345720,7 +345720,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -346025,7 +346025,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -346330,7 +346330,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -346635,7 +346635,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -346940,7 +346940,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -347245,7 +347245,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -347550,7 +347550,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -347855,7 +347855,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -348160,7 +348160,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -348465,7 +348465,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -348770,7 +348770,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -349075,7 +349075,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -349380,7 +349380,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -349685,7 +349685,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -349990,7 +349990,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -350295,7 +350295,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -350600,7 +350600,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -350905,7 +350905,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -351210,7 +351210,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -351515,7 +351515,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -351820,7 +351820,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -352125,7 +352125,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -352430,7 +352430,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -352735,7 +352735,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -353040,7 +353040,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -353345,7 +353345,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -353650,7 +353650,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -353955,7 +353955,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -354260,7 +354260,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -354565,7 +354565,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -354870,7 +354870,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -355175,7 +355175,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -355480,7 +355480,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -355785,7 +355785,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -356090,7 +356090,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -356395,7 +356395,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -356700,7 +356700,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -357005,7 +357005,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -357310,7 +357310,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -357615,7 +357615,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -357920,7 +357920,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -358225,7 +358225,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -358530,7 +358530,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -358835,7 +358835,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -359140,7 +359140,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -359445,7 +359445,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -359750,7 +359750,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -360055,7 +360055,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -360360,7 +360360,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -360665,7 +360665,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -360970,7 +360970,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -361275,7 +361275,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -361580,7 +361580,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -361885,7 +361885,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -362190,7 +362190,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -362495,7 +362495,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -362800,7 +362800,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -363105,7 +363105,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -363410,7 +363410,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -363715,7 +363715,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -364020,7 +364020,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -364325,7 +364325,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -364630,7 +364630,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -364935,7 +364935,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -365240,7 +365240,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -365545,7 +365545,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -365850,7 +365850,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -366155,7 +366155,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -366460,7 +366460,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -366765,7 +366765,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -367070,7 +367070,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -367375,7 +367375,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -367680,7 +367680,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -367985,7 +367985,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -368290,7 +368290,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -368595,7 +368595,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -368900,7 +368900,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -369205,7 +369205,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -369510,7 +369510,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -369815,7 +369815,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -370120,7 +370120,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -370425,7 +370425,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -370730,7 +370730,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -371035,7 +371035,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -371340,7 +371340,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -371645,7 +371645,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -371950,7 +371950,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -372255,7 +372255,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -372560,7 +372560,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -372865,7 +372865,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -373170,7 +373170,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -373475,7 +373475,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -373780,7 +373780,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE @@ -374085,7 +374085,7 @@ reactions { } } conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reactino represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." + details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." } workups { type: TEMPERATURE From ce26d175170829be0f5097773824e7bf5ff5585e Mon Sep 17 00:00:00 2001 From: github-actions Date: Fri, 13 Mar 2026 17:01:46 +0000 Subject: [PATCH 3/8] Update submission --- catechol_dataset_ord.pbtxt | 374237 --------------- ...set-1ec2807f02fa4beda27d2a81b86eb843.pb.gz | 3 + 2 files changed, 3 insertions(+), 374237 deletions(-) delete mode 100644 catechol_dataset_ord.pbtxt create mode 100644 data/1e/ord_dataset-1ec2807f02fa4beda27d2a81b86eb843.pb.gz diff --git a/catechol_dataset_ord.pbtxt b/catechol_dataset_ord.pbtxt deleted file mode 100644 index a018dec..0000000 --- a/catechol_dataset_ord.pbtxt +++ /dev/null @@ -1,374237 +0,0 @@ -name: "Transient flow exploration of the effect of temperature, residence time and binary solvent ratios on a uni-molecular allyl substituted catechol reaction." -description: "1,227 datapoints were collected in a series of transient flow ramps involving temperature [175 - 225 C], residence time [2 - 15 minutes] and binary solvent ratios of 24 solvents. HPLC yields reported for starting material and 2 products of the uni-molecular rearrangement of o-Bis(allyloxy)benzene. Reactions performed by SOLVE Chemistry in London (solvechemistry.com) and published in https://doi.org/10.48550/arXiv.2506.07619." -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "1" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "1" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CO" - } - identifiers { - type: NAME - value: "Methanol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "OCCO" - } - identifiers { - type: NAME - value: "Ethylene Glycol [1,2-Ethanediol]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." - } - } - } - setup { - vessel { - type: TUBE - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - material { - type: METAL - details: "stainless steel" - } - volume { - value: 7.95 - units: MILLILITER - } - } - is_automated: true - environment { - type: CUSTOM - details: "Ventilated Cabinated" - } - } - conditions { - temperature { - control { - type: CUSTOM - details: "Agilent 6890 GC oven" - } - setpoint { - value: 175.0 - units: CELSIUS - } - } - pressure { - control { - type: PRESSURIZED - details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" - } - setpoint { - value: 55.0 - units: BAR - } - } - flow { - type: PLUG_FLOW_REACTOR - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - tubing { - type: STEEL - diameter { - value: 1.0 - units: MILLIMETER - } - } - } - conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." - } - workups { - type: TEMPERATURE - details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." - temperature { - control { - type: DRY_ALUMINUM_PLATE - details: "customized cooling system made from an aluminum block and a Peltier assembly" - } - setpoint { - value: 5.0 - units: CELSIUS - } - } - is_automated: true - } - workups { - type: ALIQUOT - details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " - amount { - volume { - value: 500.0 - units: NANOLITER - } - } - is_automated: true - } - outcomes { - reaction_time { - value: 2.001019 - units: MINUTE - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=CC=C1CC=C" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 2" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 90.311775 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "1" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "1" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "2.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CO" - } - identifiers { - type: NAME - value: "Methanol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "OCCO" - } - identifiers { - type: NAME - value: "Ethylene Glycol [1,2-Ethanediol]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." - } - } - } - setup { - vessel { - type: TUBE - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - material { - type: METAL - details: "stainless steel" - } - volume { - value: 7.95 - units: MILLILITER - } - } - is_automated: true - environment { - type: CUSTOM - details: "Ventilated Cabinated" - } - } - conditions { - temperature { - control { - type: CUSTOM - details: "Agilent 6890 GC oven" - } - setpoint { - value: 175.0 - units: CELSIUS - } - } - pressure { - control { - type: PRESSURIZED - details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" - } - setpoint { - value: 55.0 - units: BAR - } - } - flow { - type: PLUG_FLOW_REACTOR - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - tubing { - type: STEEL - diameter { - value: 1.0 - units: MILLIMETER - } - } - } - conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." - } - workups { - type: TEMPERATURE - details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." - temperature { - control { - type: DRY_ALUMINUM_PLATE - details: "customized cooling system made from an aluminum block and a Peltier assembly" - } - setpoint { - value: 5.0 - units: CELSIUS - } - } - is_automated: true - } - workups { - type: ALIQUOT - details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " - amount { - volume { - value: 500.0 - units: NANOLITER - } - } - is_automated: true - } - outcomes { - reaction_time { - value: 3.9781666 - units: MINUTE - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=CC=C1CC=C" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 2" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 89.831314 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 1.3466706 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 85.69762 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 84.25732 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "1" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "2" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 3.271215 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 83.99395 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "1" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "2" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "4.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "1" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "2" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 81.930084 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 81.59716 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 4.9997964 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 80.74563 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 79.187614 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "1" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "2" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "10.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CO" - } - identifiers { - type: NAME - value: "Methanol" - } - amount { - volume { - value: 0.2247976 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "OCCO" - } - identifiers { - type: NAME - value: "Ethylene Glycol [1,2-Ethanediol]" - } - amount { - volume { - value: 0.2752024 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 77.774475 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 76.8009 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CO" - } - identifiers { - type: NAME - value: "Methanol" - } - amount { - volume { - value: 0.16507633 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "OCCO" - } - identifiers { - type: NAME - value: "Ethylene Glycol [1,2-Ethanediol]" - } - amount { - volume { - value: 0.33492365 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 76.35705 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 7.366251 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 76.32397 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "1" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "2" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "15.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CO" - } - identifiers { - type: NAME - value: "Methanol" - } - amount { - volume { - value: 0.10814692 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "OCCO" - } - identifiers { - type: NAME - value: "Ethylene Glycol [1,2-Ethanediol]" - } - amount { - volume { - value: 0.39185306 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 73.80731 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 69.59962 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "1" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "2" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "18.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 15.462058 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 69.10793 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 91.54765 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "1" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "3" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 2.4689603 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 89.96855 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 84.804596 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "1" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "3" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 77.60105 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 71.29965 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CO" - } - identifiers { - type: NAME - value: "Methanol" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "OCCO" - } - identifiers { - type: NAME - value: "Ethylene Glycol [1,2-Ethanediol]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 15.6881695 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "1" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "4" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CO" - } - identifiers { - type: NAME - value: "Methanol" - } - amount { - volume { - value: 0.056920763 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "OCCO" - } - identifiers { - type: NAME - value: "Ethylene Glycol [1,2-Ethanediol]" - } - amount { - volume { - value: 0.44307923 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 73.93163 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 75.35131 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CO" - } - identifiers { - type: NAME - value: "Methanol" - } - amount { - volume { - value: 0.13389765 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "OCCO" - } - identifiers { - type: NAME - value: "Ethylene Glycol [1,2-Ethanediol]" - } - amount { - volume { - value: 0.36610237 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 76.81182 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "1" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "4" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 6.736646 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 77.44719 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 77.74047 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "1" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "4" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "8.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CO" - } - identifiers { - type: NAME - value: "Methanol" - } - amount { - volume { - value: 0.17224985 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "OCCO" - } - identifiers { - type: NAME - value: "Ethylene Glycol [1,2-Ethanediol]" - } - amount { - volume { - value: 0.32775015 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 78.9453 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 81.50268 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "1" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "4" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "11.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 4.123347 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 82.02616 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "1" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "4" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "12.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 82.42822 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "1" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "4" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "13.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CO" - } - identifiers { - type: NAME - value: "Methanol" - } - amount { - volume { - value: 0.33492365 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "OCCO" - } - identifiers { - type: NAME - value: "Ethylene Glycol [1,2-Ethanediol]" - } - amount { - volume { - value: 0.16507633 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 82.80083 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 84.39366 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "1" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "4" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "16.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 2.774768 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "1" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "4" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "18.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 85.49586 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 85.33943 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CO" - } - identifiers { - type: NAME - value: "Methanol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "OCCO" - } - identifiers { - type: NAME - value: "Ethylene Glycol [1,2-Ethanediol]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CO" - } - identifiers { - type: NAME - value: "Methanol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "OCCO" - } - identifiers { - type: NAME - value: "Ethylene Glycol [1,2-Ethanediol]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 5.827715 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 3.5012846 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CO" - } - identifiers { - type: NAME - value: "Methanol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "OCCO" - } - identifiers { - type: NAME - value: "Ethylene Glycol [1,2-Ethanediol]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 3.2446926 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 8.939069 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 73.2139 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 33.137207 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CO" - } - identifiers { - type: NAME - value: "Methanol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "OCCO" - } - identifiers { - type: NAME - value: "Ethylene Glycol [1,2-Ethanediol]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 33.731216 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 37.382847 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "1" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "7" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "8.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CO" - } - identifiers { - type: NAME - value: "Methanol" - } - amount { - volume { - value: 0.33492365 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "OCCO" - } - identifiers { - type: NAME - value: "Ethylene Glycol [1,2-Ethanediol]" - } - amount { - volume { - value: 0.16507633 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 45.881355 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 52.75702 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 53.06451 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "1" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "9" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 50.185253 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 45.26399 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "1" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "9" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "12.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CO" - } - identifiers { - type: NAME - value: "Methanol" - } - amount { - volume { - value: 0.3149118 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "OCCO" - } - identifiers { - type: NAME - value: "Ethylene Glycol [1,2-Ethanediol]" - } - amount { - volume { - value: 0.18508817 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "1" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "9" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "17.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 6.0431786 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 6.864732 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 25.4372 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 3.814122 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "10" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." - } - } - } - setup { - vessel { - type: TUBE - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - material { - type: METAL - details: "stainless steel" - } - volume { - value: 7.95 - units: MILLILITER - } - } - is_automated: true - environment { - type: CUSTOM - details: "Ventilated Cabinated" - } - } - conditions { - temperature { - control { - type: CUSTOM - details: "Agilent 6890 GC oven" - } - setpoint { - value: 175.0 - units: CELSIUS - } - } - pressure { - control { - type: PRESSURIZED - details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" - } - setpoint { - value: 55.0 - units: BAR - } - } - flow { - type: PLUG_FLOW_REACTOR - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - tubing { - type: STEEL - diameter { - value: 1.0 - units: MILLIMETER - } - } - } - conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." - } - workups { - type: TEMPERATURE - details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." - temperature { - control { - type: DRY_ALUMINUM_PLATE - details: "customized cooling system made from an aluminum block and a Peltier assembly" - } - setpoint { - value: 5.0 - units: CELSIUS - } - } - is_automated: true - } - workups { - type: ALIQUOT - details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " - amount { - volume { - value: 500.0 - units: NANOLITER - } - } - is_automated: true - } - outcomes { - reaction_time { - value: 2.001019 - units: MINUTE - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 2.5191119 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 95.78332 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "10" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "2.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 83.24805 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "10" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 20.301706 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 57.927853 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "10" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "4.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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" - amount { - volume { - value: 500.0 - units: NANOLITER - } - } - is_automated: true - } - outcomes { - reaction_time { - value: 13.073911 - units: MINUTE - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=CC=C1CC=C" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 2" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 25.159029 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 29.716595 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 33.37325 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "10" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." - } - } - } - setup { - vessel { - type: TUBE - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - material { - type: METAL - details: "stainless steel" - } - volume { - value: 7.95 - units: MILLILITER - } - } - is_automated: true - environment { - type: CUSTOM - details: "Ventilated Cabinated" - } - } - conditions { - temperature { - control { - type: CUSTOM - details: "Agilent 6890 GC oven" - } - setpoint { - value: 175.0 - units: CELSIUS - } - } - pressure { - control { - type: PRESSURIZED - details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" - } - setpoint { - value: 55.0 - units: BAR - } - } - flow { - type: PLUG_FLOW_REACTOR - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - tubing { - type: STEEL - diameter { - value: 1.0 - units: MILLIMETER - } - } - } - conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." - } - workups { - type: TEMPERATURE - details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." - temperature { - control { - type: DRY_ALUMINUM_PLATE - details: "customized cooling system made from an aluminum block and a Peltier assembly" - } - setpoint { - value: 5.0 - units: CELSIUS - } - } - is_automated: true - } - workups { - type: ALIQUOT - details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " - amount { - volume { - value: 500.0 - units: NANOLITER - } - } - is_automated: true - } - outcomes { - reaction_time { - value: 15.011738 - units: MINUTE - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 30.17907 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 32.531654 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "11" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 31.681225 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "11" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "2.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 29.567532 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 23.636364 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 49.078278 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "11" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.38158554 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.118414454 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." - } - } - } - setup { - vessel { - type: TUBE - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - material { - type: METAL - details: "stainless steel" - } - volume { - value: 7.95 - units: MILLILITER - } - } - is_automated: true - environment { - type: CUSTOM - details: "Ventilated Cabinated" - } - } - conditions { - temperature { - control { - type: CUSTOM - details: "Agilent 6890 GC oven" - } - setpoint { - value: 175.0 - units: CELSIUS - } - } - pressure { - control { - type: PRESSURIZED - details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" - } - setpoint { - value: 55.0 - units: BAR - } - } - flow { - type: PLUG_FLOW_REACTOR - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - tubing { - type: STEEL - diameter { - value: 1.0 - units: MILLIMETER - } - } - } - conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." - } - workups { - type: TEMPERATURE - details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." - temperature { - control { - type: DRY_ALUMINUM_PLATE - details: "customized cooling system made from an aluminum block and a Peltier assembly" - } - setpoint { - value: 5.0 - units: CELSIUS - } - } - is_automated: true - } - workups { - type: ALIQUOT - details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " - amount { - volume { - value: 500.0 - units: NANOLITER - } - } - is_automated: true - } - outcomes { - reaction_time { - value: 14.989207 - units: MINUTE - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 24.093227 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 60.5542 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "11" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.34306183 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.15693817 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 62.528107 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "11" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "7.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 23.31257 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 13.702834 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 80.47101 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "11" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "10.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.26434004 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.23565996 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." - } - workups { - type: TEMPERATURE - details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." - temperature { - control { - type: DRY_ALUMINUM_PLATE - details: "customized cooling system made from an aluminum block and a Peltier assembly" - } - setpoint { - value: 5.0 - units: CELSIUS - } - } - is_automated: true - } - workups { - type: ALIQUOT - details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " - amount { - volume { - value: 500.0 - units: NANOLITER - } - } - is_automated: true - } - outcomes { - reaction_time { - value: 14.988553 - units: MINUTE - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 8.73737 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 86.072685 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "11" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "11.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.22467828 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.27532172 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 88.662186 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "11" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "12.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 4.6635056 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 3.730825 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 88.900154 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "11" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "15.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.1464952 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.3535048 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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" - amount { - volume { - value: 500.0 - units: NANOLITER - } - } - is_automated: true - } - outcomes { - reaction_time { - value: 15.007608 - units: MINUTE - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 2.48281 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 88.44024 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "11" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "16.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.10803109 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.3919689 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 89.20325 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "11" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "17.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 1.0676368 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.95071226 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 88.44288 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "11" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "20.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." - } - } - } - setup { - vessel { - type: TUBE - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - material { - type: METAL - details: "stainless steel" - } - volume { - value: 7.95 - units: MILLILITER - } - } - is_automated: true - environment { - type: CUSTOM - details: "Ventilated Cabinated" - } - } - conditions { - temperature { - control { - type: CUSTOM - details: "Agilent 6890 GC oven" - } - setpoint { - value: 175.0 - units: CELSIUS - } - } - pressure { - control { - type: PRESSURIZED - details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" - } - setpoint { - value: 55.0 - units: BAR - } - } - flow { - type: PLUG_FLOW_REACTOR - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - tubing { - type: STEEL - diameter { - value: 1.0 - units: MILLIMETER - } - } - } - conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." - } - workups { - type: TEMPERATURE - details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." - temperature { - control { - type: DRY_ALUMINUM_PLATE - details: "customized cooling system made from an aluminum block and a Peltier assembly" - } - setpoint { - value: 5.0 - units: CELSIUS - } - } - is_automated: true - } - workups { - type: ALIQUOT - details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " - amount { - volume { - value: 500.0 - units: NANOLITER - } - } - is_automated: true - } - outcomes { - reaction_time { - value: 15.017208 - units: MINUTE - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.9145041 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 87.928055 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "11" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "21.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 88.547356 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "12" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.88953644 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 87.52388 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=CC=C1CC=C" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 2" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 1.2651249 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 89.046364 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "12" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "4.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." - } - } - } - setup { - vessel { - type: TUBE - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - material { - type: METAL - details: "stainless steel" - } - volume { - value: 7.95 - units: MILLILITER - } - } - is_automated: true - environment { - type: CUSTOM - details: "Ventilated Cabinated" - } - } - conditions { - temperature { - control { - type: CUSTOM - details: "Agilent 6890 GC oven" - } - setpoint { - value: 175.0 - units: CELSIUS - } - } - pressure { - control { - type: PRESSURIZED - details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" - } - setpoint { - value: 55.0 - units: BAR - } - } - flow { - type: PLUG_FLOW_REACTOR - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - tubing { - type: STEEL - diameter { - value: 1.0 - units: MILLIMETER - } - } - } - conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." - } - workups { - type: TEMPERATURE - details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." - temperature { - control { - type: DRY_ALUMINUM_PLATE - details: "customized cooling system made from an aluminum block and a Peltier assembly" - } - setpoint { - value: 5.0 - units: CELSIUS - } - } - is_automated: true - } - workups { - type: ALIQUOT - details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " - amount { - volume { - value: 500.0 - units: NANOLITER - } - } - is_automated: true - } - outcomes { - reaction_time { - value: 8.234417 - units: MINUTE - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 1.1022186 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 88.06195 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "12" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 88.38965 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "12" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=CC=C1CC=C" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 2" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 1.0674165 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 87.96475 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "12" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "7.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=CC=C1CC=C" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 2" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.68858653 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 87.42275 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "13" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "2.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.018195167 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.48180485 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." - } - } - } - setup { - vessel { - type: TUBE - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - material { - type: METAL - details: "stainless steel" - } - volume { - value: 7.95 - units: MILLILITER - } - } - is_automated: true - environment { - type: CUSTOM - details: "Ventilated Cabinated" - } - } - conditions { - temperature { - control { - type: CUSTOM - details: "Agilent 6890 GC oven" - } - setpoint { - value: 175.0 - units: CELSIUS - } - } - pressure { - control { - type: PRESSURIZED - details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" - } - setpoint { - value: 55.0 - units: BAR - } - } - flow { - type: PLUG_FLOW_REACTOR - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - tubing { - type: STEEL - diameter { - value: 1.0 - units: MILLIMETER - } - } - } - conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." - } - workups { - type: TEMPERATURE - details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." - temperature { - control { - type: DRY_ALUMINUM_PLATE - details: "customized cooling system made from an aluminum block and a Peltier assembly" - } - setpoint { - value: 5.0 - units: CELSIUS - } - } - is_automated: true - } - workups { - type: ALIQUOT - details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " - amount { - volume { - value: 500.0 - units: NANOLITER - } - } - is_automated: true - } - outcomes { - reaction_time { - value: 14.998193 - units: MINUTE - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.8408241 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 87.752365 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "13" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.056853067 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.44314694 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 87.93605 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "13" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "4.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 1.9156073 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 3.95601 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 88.15791 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "13" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "7.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.16507633 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.33492365 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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" - amount { - volume { - value: 500.0 - units: NANOLITER - } - } - is_automated: true - } - outcomes { - reaction_time { - value: 14.988549 - units: MINUTE - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 4.386139 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 87.99897 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "13" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "8.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.17236926 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.32763073 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 87.503555 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "13" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "9.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 10.607159 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 83.91733 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "13" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "11.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 20.330442 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 64.260925 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "13" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "12.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.33100718 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.16899282 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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" - amount { - volume { - value: 500.0 - units: NANOLITER - } - } - is_automated: true - } - outcomes { - reaction_time { - value: 14.993306 - units: MINUTE - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 19.858482 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 63.34197 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "13" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "13.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.33492365 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.16507633 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 62.88421 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "13" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "14.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 20.463438 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 32.452816 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 38.046383 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "13" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "17.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.44608876 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.05391125 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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" - amount { - volume { - value: 500.0 - units: NANOLITER - } - } - is_automated: true - } - outcomes { - reaction_time { - value: 15.016259 - units: MINUTE - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 34.33017 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 34.103275 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "13" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "18.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.48467678 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.015323232 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 33.38196 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "13" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "19.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 34.66143 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 34.10189 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 33.027023 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "14" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." - } - } - } - setup { - vessel { - type: TUBE - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - material { - type: METAL - details: "stainless steel" - } - volume { - value: 7.95 - units: MILLILITER - } - } - is_automated: true - environment { - type: CUSTOM - details: "Ventilated Cabinated" - } - } - conditions { - temperature { - control { - type: CUSTOM - details: "Agilent 6890 GC oven" - } - setpoint { - value: 175.0 - units: CELSIUS - } - } - pressure { - control { - type: PRESSURIZED - details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" - } - setpoint { - value: 55.0 - units: BAR - } - } - flow { - type: PLUG_FLOW_REACTOR - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - tubing { - type: STEEL - diameter { - value: 1.0 - units: MILLIMETER - } - } - } - conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." - } - workups { - type: TEMPERATURE - details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." - temperature { - control { - type: DRY_ALUMINUM_PLATE - details: "customized cooling system made from an aluminum block and a Peltier assembly" - } - setpoint { - value: 5.0 - units: CELSIUS - } - } - is_automated: true - } - workups { - type: ALIQUOT - details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " - amount { - volume { - value: 500.0 - units: NANOLITER - } - } - is_automated: true - } - outcomes { - reaction_time { - value: 15.017208 - units: MINUTE - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 33.852085 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 32.94603 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "14" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "2.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 31.844116 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "14" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 37.262783 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 20.87241 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 36.201855 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "14" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." - } - } - } - setup { - vessel { - type: TUBE - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - material { - type: METAL - details: "stainless steel" - } - volume { - value: 7.95 - units: MILLILITER - } - } - is_automated: true - environment { - type: CUSTOM - details: "Ventilated Cabinated" - } - } - conditions { - temperature { - control { - type: CUSTOM - details: "Agilent 6890 GC oven" - } - setpoint { - value: 202.97325 - units: CELSIUS - } - } - pressure { - control { - type: PRESSURIZED - details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" - } - setpoint { - value: 55.0 - units: BAR - } - } - flow { - type: PLUG_FLOW_REACTOR - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - tubing { - type: STEEL - diameter { - value: 1.0 - units: MILLIMETER - } - } - } - conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." - } - workups { - type: TEMPERATURE - details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." - temperature { - control { - type: DRY_ALUMINUM_PLATE - details: "customized cooling system made from an aluminum block and a Peltier assembly" - } - setpoint { - value: 5.0 - units: CELSIUS - } - } - is_automated: true - } - workups { - type: ALIQUOT - details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " - amount { - volume { - value: 500.0 - units: NANOLITER - } - } - is_automated: true - } - outcomes { - reaction_time { - value: 15.017208 - units: MINUTE - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 30.243292 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "14" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "7.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "14" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "8.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 25.321484 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 27.947672 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "14" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "11.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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" - amount { - volume { - value: 500.0 - units: NANOLITER - } - } - is_automated: true - } - outcomes { - reaction_time { - value: 15.017208 - units: MINUTE - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "14" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "12.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "14" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "13.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 28.119867 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 34.904808 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 27.793634 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "15" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." - } - } - } - setup { - vessel { - type: TUBE - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - material { - type: METAL - details: "stainless steel" - } - volume { - value: 7.95 - units: MILLILITER - } - } - is_automated: true - environment { - type: CUSTOM - details: "Ventilated Cabinated" - } - } - conditions { - temperature { - control { - type: CUSTOM - details: "Agilent 6890 GC oven" - } - setpoint { - value: 225.0 - units: CELSIUS - } - } - pressure { - control { - type: PRESSURIZED - details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" - } - setpoint { - value: 55.0 - units: BAR - } - } - flow { - type: PLUG_FLOW_REACTOR - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - tubing { - type: STEEL - diameter { - value: 1.0 - units: MILLIMETER - } - } - } - conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." - } - workups { - type: TEMPERATURE - details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." - temperature { - control { - type: DRY_ALUMINUM_PLATE - details: "customized cooling system made from an aluminum block and a Peltier assembly" - } - setpoint { - value: 5.0 - units: CELSIUS - } - } - is_automated: true - } - workups { - type: ALIQUOT - details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " - amount { - volume { - value: 500.0 - units: NANOLITER - } - } - is_automated: true - } - outcomes { - reaction_time { - value: 3.828392 - units: MINUTE - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 41.14162 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 3.4187799 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "15" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "4.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "15" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 28.875895 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "15" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 25.696741 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "16" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." - } - workups { - type: TEMPERATURE - details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." - temperature { - control { - type: DRY_ALUMINUM_PLATE - details: "customized cooling system made from an aluminum block and a Peltier assembly" - } - setpoint { - value: 5.0 - units: CELSIUS - } - } - is_automated: true - } - workups { - type: ALIQUOT - details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " - amount { - volume { - value: 500.0 - units: NANOLITER - } - } - is_automated: true - } - outcomes { - reaction_time { - value: 15.007091 - units: MINUTE - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 24.928576 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "16" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "2.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.49931 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.00069002307 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 30.357801 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 43.032967 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "16" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.34489512 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.15510488 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." - } - } - } - setup { - vessel { - type: TUBE - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - material { - type: METAL - details: "stainless steel" - } - volume { - value: 7.95 - units: MILLILITER - } - } - is_automated: true - environment { - type: CUSTOM - details: "Ventilated Cabinated" - } - } - conditions { - temperature { - control { - type: CUSTOM - details: "Agilent 6890 GC oven" - } - setpoint { - value: 225.0 - units: CELSIUS - } - } - pressure { - control { - type: PRESSURIZED - details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" - } - setpoint { - value: 55.0 - units: BAR - } - } - flow { - type: PLUG_FLOW_REACTOR - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - tubing { - type: STEEL - diameter { - value: 1.0 - units: MILLIMETER - } - } - } - conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." - } - workups { - type: TEMPERATURE - details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." - temperature { - control { - type: DRY_ALUMINUM_PLATE - details: "customized cooling system made from an aluminum block and a Peltier assembly" - } - setpoint { - value: 5.0 - units: CELSIUS - } - } - is_automated: true - } - workups { - type: ALIQUOT - details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " - amount { - volume { - value: 500.0 - units: NANOLITER - } - } - is_automated: true - } - outcomes { - reaction_time { - value: 14.988549 - units: MINUTE - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 40.742104 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 7.0631857 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "16" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "7.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.33492365 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.16507633 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 6.518602 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "16" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "8.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 43.719795 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 42.87976 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 7.5184293 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "16" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "11.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.22656652 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.27343348 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." - } - workups { - type: TEMPERATURE - details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." - temperature { - control { - type: DRY_ALUMINUM_PLATE - details: "customized cooling system made from an aluminum block and a Peltier assembly" - } - setpoint { - value: 5.0 - units: CELSIUS - } - } - is_automated: true - } - workups { - type: ALIQUOT - details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " - amount { - volume { - value: 500.0 - units: NANOLITER - } - } - is_automated: true - } - outcomes { - reaction_time { - value: 14.989356 - units: MINUTE - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 44.36345 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 12.500701 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "16" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "12.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.18692161 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.3130784 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 12.093235 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "16" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "13.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 43.662384 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=CC=C1CC=C" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 2" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 33.99441 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 36.818184 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 5.946584 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "16" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "16.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.10986388 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.39013612 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." - } - } - } - setup { - vessel { - type: TUBE - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - material { - type: METAL - details: "stainless steel" - } - volume { - value: 7.95 - units: MILLILITER - } - } - is_automated: true - environment { - type: CUSTOM - details: "Ventilated Cabinated" - } - } - conditions { - temperature { - control { - type: CUSTOM - details: "Agilent 6890 GC oven" - } - setpoint { - value: 225.0 - units: CELSIUS - } - } - pressure { - control { - type: PRESSURIZED - details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" - } - setpoint { - value: 55.0 - units: BAR - } - } - flow { - type: PLUG_FLOW_REACTOR - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - tubing { - type: STEEL - diameter { - value: 1.0 - units: MILLIMETER - } - } - } - conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." - } - workups { - type: TEMPERATURE - details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." - temperature { - control { - type: DRY_ALUMINUM_PLATE - details: "customized cooling system made from an aluminum block and a Peltier assembly" - } - setpoint { - value: 5.0 - units: CELSIUS - } - } - is_automated: true - } - workups { - type: ALIQUOT - details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " - amount { - volume { - value: 500.0 - units: NANOLITER - } - } - is_automated: true - } - outcomes { - reaction_time { - value: 15.012112 - units: MINUTE - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 33.913666 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 10.245968 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "16" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "17.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.071350776 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.42864922 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 15.282176 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "16" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "18.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 20.647411 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 18.714304 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 20.498703 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "16" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "21.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." - } - workups { - type: TEMPERATURE - details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." - temperature { - control { - type: DRY_ALUMINUM_PLATE - details: "customized cooling system made from an aluminum block and a Peltier assembly" - } - setpoint { - value: 5.0 - units: CELSIUS - } - } - is_automated: true - } - workups { - type: ALIQUOT - details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " - amount { - volume { - value: 500.0 - units: NANOLITER - } - } - is_automated: true - } - outcomes { - reaction_time { - value: 15.017208 - units: MINUTE - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 18.863209 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 20.356964 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "17" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "17" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "2.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=CC=C1CC=C" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 2" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 3.3553488 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 4.225671 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 71.101395 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "17" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 14.805421 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 33.88894 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "17" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." - } - } - } - setup { - vessel { - type: TUBE - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - material { - type: METAL - details: "stainless steel" - } - volume { - value: 7.95 - units: MILLILITER - } - } - is_automated: true - environment { - type: CUSTOM - details: "Ventilated Cabinated" - } - } - conditions { - temperature { - control { - type: CUSTOM - details: "Agilent 6890 GC oven" - } - setpoint { - value: 225.0 - units: CELSIUS - } - } - pressure { - control { - type: PRESSURIZED - details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" - } - setpoint { - value: 55.0 - units: BAR - } - } - flow { - type: PLUG_FLOW_REACTOR - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - tubing { - type: STEEL - diameter { - value: 1.0 - units: MILLIMETER - } - } - } - conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." - } - workups { - type: TEMPERATURE - details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." - temperature { - control { - type: DRY_ALUMINUM_PLATE - details: "customized cooling system made from an aluminum block and a Peltier assembly" - } - setpoint { - value: 5.0 - units: CELSIUS - } - } - is_automated: true - } - workups { - type: ALIQUOT - details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " - amount { - volume { - value: 500.0 - units: NANOLITER - } - } - is_automated: true - } - outcomes { - reaction_time { - value: 11.123731 - units: MINUTE - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 16.915861 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 22.16414 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "17" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 20.346704 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "17" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "7.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=CC=C1CC=C" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 2" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 30.353472 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 17.340725 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 32.537025 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 11.988731 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "18" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.05501339 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.4449866 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." - } - } - } - setup { - vessel { - type: TUBE - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - material { - type: METAL - details: "stainless steel" - } - volume { - value: 7.95 - units: MILLILITER - } - } - is_automated: true - environment { - type: CUSTOM - details: "Ventilated Cabinated" - } - } - conditions { - temperature { - control { - type: CUSTOM - details: "Agilent 6890 GC oven" - } - setpoint { - value: 225.0 - units: CELSIUS - } - } - pressure { - control { - type: PRESSURIZED - details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" - } - setpoint { - value: 55.0 - units: BAR - } - } - flow { - type: PLUG_FLOW_REACTOR - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - tubing { - type: STEEL - diameter { - value: 1.0 - units: MILLIMETER - } - } - } - conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. 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" - amount { - volume { - value: 500.0 - units: NANOLITER - } - } - is_automated: true - } - outcomes { - reaction_time { - value: 14.99367 - units: MINUTE - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 38.035 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 12.697185 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "18" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "4.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.13217884 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.36782116 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 8.768627 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "18" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 45.179405 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 9.609975 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "18" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 42.555256 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 10.129621 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "18" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "8.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.2101551 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.2898449 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. During the transient flow ramp the flow rate ratio is adjusted to generate a ramp of solvent ratios." - } - } - } - setup { - vessel { - type: TUBE - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - material { - type: METAL - details: "stainless steel" - } - volume { - value: 7.95 - units: MILLILITER - } - } - is_automated: true - environment { - type: CUSTOM - details: "Ventilated Cabinated" - } - } - conditions { - temperature { - control { - type: CUSTOM - details: "Agilent 6890 GC oven" - } - setpoint { - value: 225.0 - units: CELSIUS - } - } - pressure { - control { - type: PRESSURIZED - details: "Average pressure reported, as it varies depending on the total flow-rate of the reaction" - } - setpoint { - value: 55.0 - units: BAR - } - } - flow { - type: PLUG_FLOW_REACTOR - details: "stainless steel coiled reactor (1.5875 mm OD, 1 mm ID, 7.95 mL volume)" - tubing { - type: STEEL - diameter { - value: 1.0 - units: MILLIMETER - } - } - } - conditions_are_dynamic: true - details: "Reaction carried out in transient flow with ramps to vary the binary solvent composition, temperature and residence time. This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." - } - workups { - type: TEMPERATURE - details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." - temperature { - control { - type: DRY_ALUMINUM_PLATE - details: "customized cooling system made from an aluminum block and a Peltier assembly" - } - setpoint { - value: 5.0 - units: CELSIUS - } - } - is_automated: true - } - workups { - type: ALIQUOT - details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " - amount { - volume { - value: 500.0 - units: NANOLITER - } - } - is_automated: true - } - outcomes { - reaction_time { - value: 14.988549 - units: MINUTE - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 40.772877 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "18" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "9.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.24982691 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.2501731 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "18" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "10.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 42.777637 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 41.444416 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "18" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "13.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.33492365 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.16507633 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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" - amount { - volume { - value: 500.0 - units: NANOLITER - } - } - is_automated: true - } - outcomes { - reaction_time { - value: 15.003771 - units: MINUTE - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 37.272987 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "18" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "14.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.36723608 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.1327639 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "18" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "15.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 25.053179 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 25.4889 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "18" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "18.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. Both solutions contain the same concentration of reactant and internal standard, but have different solvents. 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This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." - } - workups { - type: TEMPERATURE - details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." - temperature { - control { - type: DRY_ALUMINUM_PLATE - details: "customized cooling system made from an aluminum block and a Peltier assembly" - } - setpoint { - value: 5.0 - units: CELSIUS - } - } - is_automated: true - } - workups { - type: ALIQUOT - details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. " - amount { - volume { - value: 500.0 - units: NANOLITER - } - } - is_automated: true - } - outcomes { - reaction_time { - value: 15.017208 - units: MINUTE - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 27.140732 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "2" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "18" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "19.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C(C(F)(F)F)(C(F)(F)F)O" - } - identifiers { - type: NAME - value: "1,1,1,3,3,3-Hexafluoropropan-2-ol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O1C(C)CCC1" - } - identifiers { - type: NAME - value: "2-Methyltetrahydrofuran [2-MeTHF]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 27.710579 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 92.29603 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "19" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "2.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 92.144005 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "19" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 92.25244 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "19" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "4.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 88.88638 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "19" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 87.48093 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "19" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 86.734474 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "20" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 84.38013 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "20" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "2.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.49751475 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.0024852501 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 85.19077 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "20" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 86.68076 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 88.08293 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "20" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.38163328 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.118366726 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 89.519035 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "20" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "8.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.7693835 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "20" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "10.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 94.63352 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 95.11854 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "20" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "13.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 1.1138337 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "20" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "15.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.14654279 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.3534572 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 96.40476 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 97.23426 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "20" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "18.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 1.5631973 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 96.7592 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "20" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "19.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 1.6133546 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 96.84827 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "21" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 96.97397 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 96.62079 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "21" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "4.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 1.1561208 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 95.86702 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "21" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 94.82092 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "21" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "9.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.81815743 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 94.69428 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "21" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "11.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.2803707 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.21962929 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 93.17054 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 92.43759 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "21" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "14.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 92.0311 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "21" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "16.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.39687037 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.10312963 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 88.73408 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 85.60097 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "21" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "18.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 82.841034 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "21" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "19.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 82.104164 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "21" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "20.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 82.71462 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "21" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "21.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 83.795456 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "22" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." - } - workups { - type: TEMPERATURE - details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." - temperature { - control { - type: DRY_ALUMINUM_PLATE - details: "customized cooling system made from an aluminum block and a Peltier assembly" - } - setpoint { - value: 5.0 - units: CELSIUS - } - } - is_automated: true - } - workups { - type: ALIQUOT - details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 83.32556 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "22" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "2.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 83.52969 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "22" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 82.87027 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "22" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "4.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.59451205 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 76.63809 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "22" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 67.407036 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "22" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 54.331802 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "22" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "7.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 39.980015 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "22" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "8.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 10.587948 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 31.619055 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "22" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "9.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 11.10779 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 28.245901 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "22" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "10.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 25.911667 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "22" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "11.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 23.556625 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "22" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "12.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 25.228146 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "22" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "13.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 8.5378275 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 24.906404 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "22" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "14.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 8.362453 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 25.289581 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "22" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "15.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 7.800649 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 22.925522 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "22" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "16.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 23.910723 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "22" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "17.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 24.730686 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "22" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "18.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 8.451737 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 27.019402 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "23" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 17.802305 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 28.168919 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "23" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "2.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.46527869 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.034721322 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 26.10105 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 23.630808 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "23" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 33.827362 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 24.591888 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 33.83458 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 24.6481 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "23" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "7.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.33492365 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.16507633 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 24.019894 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 20.562538 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "23" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "10.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 40.971825 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 39.463165 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "23" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "12.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 18.87398 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 16.46635 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "23" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "15.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 42.796726 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "23" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "17.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 13.341183 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "23" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "18.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 13.331798 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "24" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 14.112561 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 43.127934 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "24" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "4.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 17.94274 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 18.48394 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "24" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "7.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 40.479763 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 18.817009 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "24" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "8.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 38.967728 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "24" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "9.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.19442485 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.30557513 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 21.03907 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 24.382736 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "24" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "12.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 35.56215 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "24" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "13.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 23.70262 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "24" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "14.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.33492365 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.16507633 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 24.613047 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 27.31098 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 18.376486 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 30.236822 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "24" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "19.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 26.47246 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "24" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "20.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 23.539667 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "24" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "21.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "C1CCCCC1" - } - identifiers { - type: NAME - value: "Cyclohexane" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC(O)C" - } - identifiers { - type: NAME - value: "IPA [Propan-2-ol]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 25.027203 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "3" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "24" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "22.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 8.622531 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 86.20899 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "25" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "2.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "O.CC#N" - } - identifiers { - type: NAME - value: "Water.Acetonitrile" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC#N" - } - identifiers { - type: NAME - value: "Acetonitrile" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 94.656654 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "25" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "O.CC#N" - } - identifiers { - type: NAME - value: "Water.Acetonitrile" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC#N" - } - identifiers { - type: NAME - value: "Acetonitrile" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 89.869484 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "25" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "4.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "O.CC#N" - } - identifiers { - type: NAME - value: "Water.Acetonitrile" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC#N" - } - identifiers { - type: NAME - value: "Acetonitrile" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 84.46417 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "25" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 10.575115 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 75.351036 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 73.698875 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "26" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 82.29808 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 6.9433928 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 88.49821 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 95.12487 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 98.44036 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "26" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "21.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 99.220024 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "27" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "O.CC#N" - } - identifiers { - type: NAME - value: "Water.Acetonitrile" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC#N" - } - identifiers { - type: NAME - value: "Acetonitrile" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 98.99385 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "27" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "2.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "O.CC#N" - } - identifiers { - type: NAME - value: "Water.Acetonitrile" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC#N" - } - identifiers { - type: NAME - value: "Acetonitrile" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 99.09418 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 99.25654 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 99.35251 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "27" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 99.0432 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "27" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "O.CC#N" - } - identifiers { - type: NAME - value: "Water.Acetonitrile" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC#N" - } - identifiers { - type: NAME - value: "Acetonitrile" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 99.00549 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "27" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "7.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "O.CC#N" - } - identifiers { - type: NAME - value: "Water.Acetonitrile" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC#N" - } - identifiers { - type: NAME - value: "Acetonitrile" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 97.14299 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 94.42425 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 5.420645 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "28" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "13.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 87.87429 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 74.97649 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "28" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "19.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "O.CC#N" - } - identifiers { - type: NAME - value: "Water.Acetonitrile" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC#N" - } - identifiers { - type: NAME - value: "Acetonitrile" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "28" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "20.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "O.CC#N" - } - identifiers { - type: NAME - value: "Water.Acetonitrile" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC#N" - } - identifiers { - type: NAME - value: "Acetonitrile" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "29" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "2.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 73.57623 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "29" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "O.CC#N" - } - identifiers { - type: NAME - value: "Water.Acetonitrile" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC#N" - } - identifiers { - type: NAME - value: "Acetonitrile" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 61.738228 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "29" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "4.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "O.CC#N" - } - identifiers { - type: NAME - value: "Water.Acetonitrile" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC#N" - } - identifiers { - type: NAME - value: "Acetonitrile" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 33.818604 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "29" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 39.091087 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "O.CC#N" - } - identifiers { - type: NAME - value: "Water.Acetonitrile" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC#N" - } - identifiers { - type: NAME - value: "Acetonitrile" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "O.CC#N" - } - identifiers { - type: NAME - value: "Water.Acetonitrile" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC#N" - } - identifiers { - type: NAME - value: "Acetonitrile" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "O.CC#N" - } - identifiers { - type: NAME - value: "Water.Acetonitrile" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC#N" - } - identifiers { - type: NAME - value: "Acetonitrile" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "30" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "O.CC#N" - } - identifiers { - type: NAME - value: "Water.Acetonitrile" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC#N" - } - identifiers { - type: NAME - value: "Acetonitrile" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 4.537611 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "30" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "4.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "O.CC#N" - } - identifiers { - type: NAME - value: "Water.Acetonitrile" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC#N" - } - identifiers { - type: NAME - value: "Acetonitrile" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "30" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "O.CC#N" - } - identifiers { - type: NAME - value: "Water.Acetonitrile" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC#N" - } - identifiers { - type: NAME - value: "Acetonitrile" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "30" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "O.CC#N" - } - identifiers { - type: NAME - value: "Water.Acetonitrile" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC#N" - } - identifiers { - type: NAME - value: "Acetonitrile" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 39.328926 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 33.159683 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 1.1052915 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 2.298289 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 29.967669 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 9.884384 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "31" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "18.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 11.486905 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "32" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 14.448528 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "32" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "2.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "O.CC#N" - } - identifiers { - type: NAME - value: "Water.Acetonitrile" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC#N" - } - identifiers { - type: NAME - value: "Acetonitrile" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 84.29281 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "32" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "O.CC#N" - } - identifiers { - type: NAME - value: "Water.Acetonitrile" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC#N" - } - identifiers { - type: NAME - value: "Acetonitrile" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 26.919603 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 15.143082 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "32" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "O.CC#N" - } - identifiers { - type: NAME - value: "Water.Acetonitrile" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC#N" - } - identifiers { - type: NAME - value: "Acetonitrile" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 14.566842 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "32" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "7.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "O.CC#N" - } - identifiers { - type: NAME - value: "Water.Acetonitrile" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC#N" - } - identifiers { - type: NAME - value: "Acetonitrile" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 14.855659 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "33" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "O.CC#N" - } - identifiers { - type: NAME - value: "Water.Acetonitrile" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC#N" - } - identifiers { - type: NAME - value: "Acetonitrile" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 13.202613 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "33" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "4.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 1.6080221 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.94460833 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "33" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "7.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 32.980995 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.51529515 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "O.CC#N" - } - identifiers { - type: NAME - value: "Water.Acetonitrile" - } - amount { - volume { - value: 0.2496826 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC#N" - } - identifiers { - type: NAME - value: "Acetonitrile" - } - amount { - volume { - value: 0.2503174 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 31.99132 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "33" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "19.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "33" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "20.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "O.CC#N" - } - identifiers { - type: NAME - value: "Water.Acetonitrile" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC#N" - } - identifiers { - type: NAME - value: "Acetonitrile" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "4" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "33" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "21.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "O.CC#N" - } - identifiers { - type: NAME - value: "Water.Acetonitrile" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CC#N" - } - identifiers { - type: NAME - value: "Acetonitrile" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 99.72242 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 99.00568 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "5" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "35" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 99.196396 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.6843647 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "5" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "35" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 96.75059 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "5" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "35" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "9.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 1.2824466 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "5" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "35" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "11.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 93.63607 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "5" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "35" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "14.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 1.6758835 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "5" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "35" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "16.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 90.14844 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 87.75985 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.91133815 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 94.34474 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "5" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "36" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 90.550804 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 88.11197 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 2.9703789 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "5" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "37" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 91.18863 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 92.86368 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "5" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "37" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 2.2260847 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "5" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "37" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "8.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 94.6799 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 96.36474 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "5" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "37" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "11.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 1.2591345 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "5" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "37" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "13.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 97.48715 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 98.9282 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "5" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "37" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "16.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 99.726715 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 99.50566 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 24.937365 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 15.409601 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 14.825089 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "5" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "39" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "4.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 36.135796 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 15.358029 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 16.010937 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "5" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "40" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "2.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 15.34609 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 5.819968 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "5" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "40" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.9907528 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "5" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "40" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "5" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "40" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "7.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "5" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "40" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "10.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 1.2240055 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "5" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "40" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "12.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "5" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "40" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "15.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "5" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "41" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 2.1279836 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "5" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "42" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "7.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 2.5401564 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "5" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "42" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "9.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "5" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "42" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "12.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 2.6707447 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "5" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "42" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "14.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 8.871884 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "5" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "42" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "17.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 29.036518 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 14.436194 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 90.0724 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.68387294 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 90.5466 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 91.503586 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "6" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "44" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.6206555 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 92.09268 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 91.8053 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 92.86933 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "6" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "44" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "10.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.3793704 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 93.2368 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "6" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "44" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "12.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 94.967735 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 94.80861 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 98.65359 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 99.51267 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "6" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "44" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "20.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 98.80676 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 99.10284 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "6" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "45" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "4.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "6" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "45" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 98.812416 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 99.0125 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "6" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "46" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 95.82361 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 95.121346 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "6" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "46" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "7.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.3407468 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 93.21336 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 91.87557 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "6" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "46" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "12.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.6403043 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.7208843 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.8040796 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 89.60232 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 13.216835 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 20.125826 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 8.020526 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 30.059366 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 19.132486 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 25.627861 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 27.11916 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "6" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "49" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 19.294722 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 33.990406 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "6" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "49" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "11.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 18.038286 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "6" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "49" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "13.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 41.76699 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 16.849674 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 16.556625 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 60.296116 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "6" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "50" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 13.210106 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 67.956345 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 61.991062 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "6" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "51" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 12.778156 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 45.733864 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 37.17276 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "6" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "51" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "8.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 17.575653 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 29.388218 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 18.355202 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 23.928478 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 21.663237 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "6" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "51" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "18.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 18.71293 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 85.45568 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 65.49714 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "7" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "52" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 11.325203 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 64.35312 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 67.4592 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "7" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "53" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC(F)(F)F" - } - identifiers { - type: NAME - value: "2,2,2-Trifluoroethanol" - } - amount { - volume { - value: 0.3818967 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O.OCC(F)(F)F" - } - identifiers { - type: NAME - value: "Water.2,2,2-Trifluoroethanol" - } - amount { - volume { - value: 0.1181033 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 10.074772 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 67.87669 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 65.125694 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "7" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "53" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "10.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 14.981883 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "7" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "53" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "12.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 61.648647 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 64.834175 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "7" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "53" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "15.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC(F)(F)F" - } - identifiers { - type: NAME - value: "2,2,2-Trifluoroethanol" - } - amount { - volume { - value: 0.14698848 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O.OCC(F)(F)F" - } - identifiers { - type: NAME - value: "Water.2,2,2-Trifluoroethanol" - } - amount { - volume { - value: 0.35301152 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 17.730616 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 54.908966 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 18.170902 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "7" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "54" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 53.02564 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 92.65786 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "7" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "54" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "4.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 9.73642 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 78.19622 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "7" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "54" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 53.46406 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 57.559742 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "7" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "55" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "2.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 18.126753 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "7" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "55" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "4.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 59.25781 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 60.46145 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 65.85212 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "7" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "55" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "7.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC(F)(F)F" - } - identifiers { - type: NAME - value: "2,2,2-Trifluoroethanol" - } - amount { - volume { - value: 0.16507633 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O.OCC(F)(F)F" - } - identifiers { - type: NAME - value: "Water.2,2,2-Trifluoroethanol" - } - amount { - volume { - value: 0.33492365 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 13.069418 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 66.783806 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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" - amount { - volume { - value: 500.0 - units: NANOLITER - } - } - is_automated: true - } - outcomes { - reaction_time { - value: 14.990215 - units: MINUTE - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 69.51141 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "7" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "55" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "12.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC(F)(F)F" - } - identifiers { - type: NAME - value: "2,2,2-Trifluoroethanol" - } - amount { - volume { - value: 0.33068734 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O.OCC(F)(F)F" - } - identifiers { - type: NAME - value: "Water.2,2,2-Trifluoroethanol" - } - amount { - volume { - value: 0.16931267 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 12.480912 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 66.31886 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 71.44949 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 67.956726 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "7" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "55" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "17.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 11.202337 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 46.204144 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 5.9325952e-08 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "7" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "56" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "11.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "7" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "56" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "12.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "7" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "56" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "13.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 40.168957 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "7" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "57" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 12.529473 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "7" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "58" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 3.3722196 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 5.7414217 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "7" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "58" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC(F)(F)F" - } - identifiers { - type: NAME - value: "2,2,2-Trifluoroethanol" - } - amount { - volume { - value: 0.34520587 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O.OCC(F)(F)F" - } - identifiers { - type: NAME - value: "Water.2,2,2-Trifluoroethanol" - } - amount { - volume { - value: 0.15479413 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 15.284375 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 7.93083 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 9.199994 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 9.703064 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 9.111252 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "7" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "58" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "11.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC(F)(F)F" - } - identifiers { - type: NAME - value: "2,2,2-Trifluoroethanol" - } - amount { - volume { - value: 0.2268866 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O.OCC(F)(F)F" - } - identifiers { - type: NAME - value: "Water.2,2,2-Trifluoroethanol" - } - amount { - volume { - value: 0.2731134 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 23.054035 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 6.943593 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 4.81053 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 2.8889704 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "7" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "58" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "16.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC(F)(F)F" - } - identifiers { - type: NAME - value: "2,2,2-Trifluoroethanol" - } - amount { - volume { - value: 0.11017452 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O.OCC(F)(F)F" - } - identifiers { - type: NAME - value: "Water.2,2,2-Trifluoroethanol" - } - amount { - volume { - value: 0.38982546 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 23.871878 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 3.4936068 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.8279913 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 26.156118 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 6.583602 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 29.301468 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "7" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "60" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC(F)(F)F" - } - identifiers { - type: NAME - value: "2,2,2-Trifluoroethanol" - } - amount { - volume { - value: 0.05451758 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O.OCC(F)(F)F" - } - identifiers { - type: NAME - value: "Water.2,2,2-Trifluoroethanol" - } - amount { - volume { - value: 0.44548243 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 21.56761 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "7" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "60" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "8.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 17.832424 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "7" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "60" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "13.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC(F)(F)F" - } - identifiers { - type: NAME - value: "2,2,2-Trifluoroethanol" - } - amount { - volume { - value: 0.33492365 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "O.OCC(F)(F)F" - } - identifiers { - type: NAME - value: "Water.2,2,2-Trifluoroethanol" - } - amount { - volume { - value: 0.16507633 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 11.56032 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 89.958305 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "61" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "2.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 90.093704 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "61" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CN(C)C(C)=O" - } - identifiers { - type: NAME - value: "DMA [N,N-Dimethylacetamide]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CCCCCCCCCCO" - } - identifiers { - type: NAME - value: "Decanol" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 90.25318 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 90.88666 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 90.600975 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "61" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 91.66614 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 89.79997 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "62" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "2.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CN(C)C(C)=O" - } - identifiers { - type: NAME - value: "DMA [N,N-Dimethylacetamide]" - } - amount { - volume { - value: 0.4974471 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CCCCCCCCCCO" - } - identifiers { - type: NAME - value: "Decanol" - } - amount { - volume { - value: 0.0025528914 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 92.22385 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 91.564705 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "62" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "4.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CN(C)C(C)=O" - } - identifiers { - type: NAME - value: "DMA [N,N-Dimethylacetamide]" - } - amount { - volume { - value: 0.42014122 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CCCCCCCCCCO" - } - identifiers { - type: NAME - value: "Decanol" - } - amount { - volume { - value: 0.079858795 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 90.84891 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "62" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 90.49835 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "62" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 88.49363 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "62" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "7.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 90.717384 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 91.86684 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 91.146835 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "62" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "10.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 89.90026 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "62" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "11.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 91.52447 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "62" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "12.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CN(C)C(C)=O" - } - identifiers { - type: NAME - value: "DMA [N,N-Dimethylacetamide]" - } - amount { - volume { - value: 0.18501401 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CCCCCCCCCCO" - } - identifiers { - type: NAME - value: "Decanol" - } - amount { - volume { - value: 0.314986 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 92.00497 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "62" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "15.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.5321128 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "62" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "17.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 84.14198 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 1.3165346 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "63" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 90.95014 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 91.4121 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CN(C)C(C)=O" - } - identifiers { - type: NAME - value: "DMA [N,N-Dimethylacetamide]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CCCCCCCCCCO" - } - identifiers { - type: NAME - value: "Decanol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 83.56479 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "63" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "4.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 90.400375 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "63" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 91.72411 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "64" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CN(C)C(C)=O" - } - identifiers { - type: NAME - value: "DMA [N,N-Dimethylacetamide]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CCCCCCCCCCO" - } - identifiers { - type: NAME - value: "Decanol" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 90.95776 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 90.54094 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 91.217896 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "64" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "4.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 91.41469 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "64" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.48832121 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 90.39494 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "64" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CN(C)C(C)=O" - } - identifiers { - type: NAME - value: "DMA [N,N-Dimethylacetamide]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CCCCCCCCCCO" - } - identifiers { - type: NAME - value: "Decanol" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 91.09412 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "64" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "7.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 88.77397 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CN(C)C(C)=O" - } - identifiers { - type: NAME - value: "DMA [N,N-Dimethylacetamide]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CCCCCCCCCCO" - } - identifiers { - type: NAME - value: "Decanol" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "65" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 91.00521 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 81.396805 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "65" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 11.775189 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 28.473764 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "65" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "8.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CN(C)C(C)=O" - } - identifiers { - type: NAME - value: "DMA [N,N-Dimethylacetamide]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CCCCCCCCCCO" - } - identifiers { - type: NAME - value: "Decanol" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 13.285815 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 6.364098 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "65" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "11.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 20.704601 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 6.23334 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "65" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "13.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 6.422868 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "66" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 15.175844 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 45.020355 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "66" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "4.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 21.191212 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "66" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CN(C)C(C)=O" - } - identifiers { - type: NAME - value: "DMA [N,N-Dimethylacetamide]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CCCCCCCCCCO" - } - identifiers { - type: NAME - value: "Decanol" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 9.204754 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "66" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 6.6556973 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 6.647432 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 22.703762 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 6.8499627 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "67" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "2.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 7.7293887 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "67" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CN(C)C(C)=O" - } - identifiers { - type: NAME - value: "DMA [N,N-Dimethylacetamide]" - } - amount { - volume { - value: 0.44542244 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CCCCCCCCCCO" - } - identifiers { - type: NAME - value: "Decanol" - } - amount { - volume { - value: 0.05457755 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 6.439114 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 6.594581 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "67" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CN(C)C(C)=O" - } - identifiers { - type: NAME - value: "DMA [N,N-Dimethylacetamide]" - } - amount { - volume { - value: 0.36825582 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CCCCCCCCCCO" - } - identifiers { - type: NAME - value: "Decanol" - } - amount { - volume { - value: 0.13174418 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 6.69648 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "67" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 33.93602 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 5.935101 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "67" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "7.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "67" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "8.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 6.3241887 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 6.2802362 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CN(C)C(C)=O" - } - identifiers { - type: NAME - value: "DMA [N,N-Dimethylacetamide]" - } - amount { - volume { - value: 0.25062054 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CCCCCCCCCCO" - } - identifiers { - type: NAME - value: "Decanol" - } - amount { - volume { - value: 0.24937946 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 6.111543 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "67" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "11.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 34.05263 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 5.150175 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "67" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "13.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 4.0060544 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CN(C)C(C)=O" - } - identifiers { - type: NAME - value: "DMA [N,N-Dimethylacetamide]" - } - amount { - volume { - value: 0.13319774 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CCCCCCCCCCO" - } - identifiers { - type: NAME - value: "Decanol" - } - amount { - volume { - value: 0.36680228 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "67" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "16.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 34.457592 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "67" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "18.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "68" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "2.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 77.951904 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "68" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 40.719006 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 19.142237 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "68" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 35.8545 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 9.433005 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "68" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "68" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "7.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CN(C)C(C)=O" - } - identifiers { - type: NAME - value: "DMA [N,N-Dimethylacetamide]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CCCCCCCCCCO" - } - identifiers { - type: NAME - value: "Decanol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "69" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "2.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 34.413307 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "69" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "69" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "4.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CN(C)C(C)=O" - } - identifiers { - type: NAME - value: "DMA [N,N-Dimethylacetamide]" - } - amount { - volume { - value: 0.10879952 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CCCCCCCCCCO" - } - identifiers { - type: NAME - value: "Decanol" - } - amount { - volume { - value: 0.39120048 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 0.0 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 5.289206 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "69" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "7.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 33.428722 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 3.6423755 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "69" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "8.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 5.282382 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "69" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "9.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CN(C)C(C)=O" - } - identifiers { - type: NAME - value: "DMA [N,N-Dimethylacetamide]" - } - amount { - volume { - value: 0.22576651 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CCCCCCCCCCO" - } - identifiers { - type: NAME - value: "Decanol" - } - amount { - volume { - value: 0.2742335 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 4.779566 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 5.161997 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "CN(C)C(C)=O" - } - identifiers { - type: NAME - value: "DMA [N,N-Dimethylacetamide]" - } - amount { - volume { - value: 0.30508116 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "CCCCCCCCCCO" - } - identifiers { - type: NAME - value: "Decanol" - } - amount { - volume { - value: 0.19491883 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 5.522212 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "69" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "12.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 30.697922 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "69" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "13.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 5.6284466 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 6.294883 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "69" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "17.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 22.409094 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 6.5041637 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "69" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "18.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "69" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "19.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 6.7691536 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "8" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "69" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "20.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 6.8383827 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "70" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 90.32306 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 92.20332 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "70" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 91.34245 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "70" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "4.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 90.17245 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "70" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.72921443 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "71" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "2.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 89.62035 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 84.55357 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "71" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 1.4175376 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 87.64845 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 82.69364 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "71" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "10.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.6039203 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 86.316795 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "71" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "12.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 85.664734 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 85.40783 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.45176515 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 85.667725 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 85.66272 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "71" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "17.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 93.27575 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "72" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 92.87838 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "72" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "2.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 92.46234 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "72" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 95.07492 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "72" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "4.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 92.516815 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "72" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 90.86054 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "72" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." - } - workups { - type: TEMPERATURE - details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." - temperature { - control { - type: DRY_ALUMINUM_PLATE - details: "customized cooling system made from an aluminum block and a Peltier assembly" - } - setpoint { - value: 5.0 - units: CELSIUS - } - } - is_automated: true - } - workups { - type: ALIQUOT - details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 89.68427 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "72" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "7.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 89.97549 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "73" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 87.73732 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "73" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 83.357414 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "73" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "4.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.09535354 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.40464646 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 85.31972 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.13372463 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.36627537 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 88.723564 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "73" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.29036945 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 88.57825 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "73" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "8.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 88.93471 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 94.00786 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "73" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "11.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.6917448 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 91.15621 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "73" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "13.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 107.13868 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 95.82321 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.6975332 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 97.24839 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "74" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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This reaction represents a single HPLC measurement sampled from within a transient flow ramp. Conditions are an estimate of what the reaction sample was exposed to prior to analysis." - } - workups { - type: TEMPERATURE - details: "The solution flowed through a customized cooling system made from an aluminum block and a Peltier assembly to quench the reaction." - temperature { - control { - type: DRY_ALUMINUM_PLATE - details: "customized cooling system made from an aluminum block and a Peltier assembly" - } - setpoint { - value: 5.0 - units: CELSIUS - } - } - is_automated: true - } - workups { - type: ALIQUOT - details: "A Vici 4 port 2 position sampling valve sampled small aliquots (500 nL) into the HPLC for online analysis measurements of the reaction. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 100.00001 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "74" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "2.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 83.35871 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 84.87891 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 82.69794 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "74" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 81.74561 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "74" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "74" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "8.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.52881867 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "74" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "9.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "75" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 80.99506 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "75" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "2.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 80.88445 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "75" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "75" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 36.860653 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "75" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "7.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 14.462351 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "75" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "8.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "75" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "9.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 33.647377 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 4.9152 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "75" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "11.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 4.954248 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "75" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "12.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 4.9176884 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "75" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "13.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Temperature Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 5.11656 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "76" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 34.036457 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 5.055804 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 68.05385 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "76" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 29.267397 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "76" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "4.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 11.034118 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "76" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 5.139076 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "76" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 33.49574 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 4.9850206 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "76" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "7.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "77" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 7.245657 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 7.6817193 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "77" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "4.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 37.493824 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 8.596843 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "77" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 9.194935 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "77" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 8.86458 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 10.655576 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "77" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "9.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 33.112423 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 11.82765 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "77" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "10.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 13.319677 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "77" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "11.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 14.264569 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 14.232551 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "77" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "14.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 28.349241 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 18.878252 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 21.556171 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "77" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "19.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 17.408821 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "77" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "21.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 20.618477 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "78" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 20.348885 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "78" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "2.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "78" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 6.257975 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 67.61102 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 45.118977 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "78" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 29.685944 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "78" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 20.094847 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "78" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "7.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 20.093584 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "78" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "8.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 16.54086 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 19.713734 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "79" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "2.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 16.498722 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 16.304604 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 14.895531 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "79" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 30.063824 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 13.841266 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 12.185154 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "79" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "10.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 37.592274 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 10.249585 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "79" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "12.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 15.818915 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 9.494016 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 43.083775 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 7.8205013 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "79" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "18.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 11.738352 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "79" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "19.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: REACTANT - is_limiting: true - preparations { - } - } - components { - identifiers { - type: SMILES - value: "OCC" - } - identifiers { - type: NAME - value: "Ethanol" - } - amount { - volume { - value: 0.5 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - value: "C1CCOC1" - } - identifiers { - type: NAME - value: "THF [Tetrahydrofuran]" - } - amount { - volume { - value: 0.0 - units: MICROLITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "ethyl benzene" - value: "CCc1ccccc1" - } - amount { - volume { - value: 0.1 - units: NANOLITER - } - volume_includes_solutes: false - } - reaction_role: INTERNAL_STANDARD - } - addition_device { - type: PISTON_PUMP - details: "Two solutions are combined by Knauer Azure 4.1S piston pumps fitted with stainless steel 10 mL pump heads. 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 11.980319 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "9" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "79" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "20.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Solvent Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 42.918964 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "10" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "80" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 12.998896 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 56.38153 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "10" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "80" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "11.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 16.939034 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 57.082973 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "10" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "81" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "3.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 78.17703 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 68.79549 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "10" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "81" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 4.342286 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 66.17401 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "10" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "81" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "16.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 4.466738 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 65.50108 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "11" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "82" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 5.2117286 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.61817765 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "11" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "83" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "4.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 70.92459 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 67.98609 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 4.6421175 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 4.480465 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "12" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "84" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 87.70786 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 78.17443 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "12" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "84" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "4.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 4.917637 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 66.08776 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 65.2502 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "12" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "84" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "9.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 6.5895915 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 66.18797 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "12" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "84" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "14.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 8.569548 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 71.6226 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 66.44585 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "12" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "85" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "1.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 0.0 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 92.04205 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "12" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "85" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "6.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 3.2086117 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 84.85233 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "12" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "85" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "11.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 3.579833 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 87.151085 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 85.39314 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "12" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "85" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "16.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 3.6464987 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 86.7829 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "13" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "86" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 69.61085 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "13" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "86" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "10.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 70.37609 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 69.874855 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 64.78715 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "13" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "87" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "5.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 15.611496 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "13" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "87" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "7.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 59.987186 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 59.519577 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "13" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "87" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "10.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 15.918773 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "13" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "87" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "12.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 61.025158 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - 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} - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 16.04065 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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} - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} -reactions { - identifiers { - type: CUSTOM - details: "EXP NUM - Experiment index; all rows with the same EXP NUM were performed on the same automated experimental run where a set of transient flow ramps were performed on temperature, residence time, and two solvent ratios." - value: "13" - } - identifiers { - type: CUSTOM - details: "RAMP NUM - Ramp number" - value: "87" - } - identifiers { - type: CUSTOM - details: "DATA POINT - index of the reactions within an individual ramp" - value: "17.0" - } - identifiers { - type: CUSTOM - details: "RAMP DESCRIPTION - Description of the ramp" - value: "Residence Time Ramp" - } - inputs { - key: "Combined flow" - value { - components { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510292D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 8.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -6.6813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -5.8152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7023 -5.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2023 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -8.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7023 -7.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - 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" - amount { - volume { - value: 500.0 - units: NANOLITER - } - } - is_automated: true - } - outcomes { - reaction_time { - value: 15.017208 - units: MINUTE - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510442D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 16.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -5.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -4.2322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9273 -5.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4273 -6.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 2 0 0 0 0\n 11 2 1 0 0 0 0\n 11 12 1 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=CC=C1CC=C" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 2" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.222) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 14.95753 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510492D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.0523 -7.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0523 -5.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -6.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -5.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0523 -7.6973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5523 -8.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0 0 0 0\n 2 3 2 0 0 0 0\n 3 4 1 0 0 0 0\n 3 5 1 0 0 0 0\n 5 6 1 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 2 0 0 0 0\n 5 9 2 0 0 0 0\n 9 10 1 0 0 0 0\n 10 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 9 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 2 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "OC1=C(O)C(CC=C)=C(CC=C)C=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "Product 3" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.361) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - percentage { - value: 15.552541 - } - } - reaction_role: PRODUCT - } - products { - identifiers { - type: MOLBLOCK - details: "Drawn with Ketcher" - value: "\n -INDIGO-12192510502D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 12.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -6.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -5.9152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6273 -5.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1273 -5.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1273 -8.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6273 -7.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0 0 0 0\n 2 3 1 0 0 0 0\n 3 4 1 0 0 0 0\n 4 5 1 0 0 0 0\n 5 6 2 0 0 0 0\n 6 7 1 0 0 0 0\n 7 8 1 0 0 0 0\n 8 9 1 0 0 0 0\n 9 10 2 0 0 0 0\n 6 11 1 0 0 0 0\n 11 12 2 0 0 0 0\n 12 13 1 0 0 0 0\n 13 14 2 0 0 0 0\n 14 5 1 0 0 0 0\nM END\n" - } - identifiers { - type: SMILES - value: "C=CCOC1=C(OCC=C)C=CC=C1" - } - identifiers { - type: CUSTOM - details: "label from associated paper and datasets" - value: "SM" - } - measurements { - analysis_key: "HPLC" - type: YIELD - details: "yield = response factor (0.525) x peak ratio x concentration of IS / concentration of reactant in input" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - percentage { - value: 61.570576 - } - } - reaction_role: REACTANT - } - analyses { - key: "HPLC" - value { - type: LC - details: "Agilent 1290 UPLC" - is_of_isolated_species: false - instrument_manufacturer: "Agilent" - } - } - } - provenance { - experimenter { - name: "Sarah Boyall" - orcid: "0000-0001-5049-8335" - organization: "SOLVE Chemistry" - email: "sarah@solvechemistry.com" - } - city: "London" - experiment_start { - value: "2025-01-01T00:00:00" - } - publication_url: "https://arxiv.org/abs/2506.07619" - record_created { - time { - value: "2025-12-19T10:27:58" - } - person { - name: "Jose Pablo Folch" - orcid: "0000-0003-2586-4959" - organization: "SOLVE Chemistry" - email: "jose@solvechemistry.com" - } - } - } -} diff --git a/data/1e/ord_dataset-1ec2807f02fa4beda27d2a81b86eb843.pb.gz b/data/1e/ord_dataset-1ec2807f02fa4beda27d2a81b86eb843.pb.gz new file mode 100644 index 0000000..2c4d68a --- /dev/null +++ b/data/1e/ord_dataset-1ec2807f02fa4beda27d2a81b86eb843.pb.gz @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:4ad15c3d5e56b95d26fba1aadc2761903aecae9b15b1793d2a52d52ec996ce18 +size 146316 From d588cde1a0875555c8c1a233bd679942691c1156 Mon Sep 17 00:00:00 2001 From: github-actions Date: Fri, 13 Mar 2026 17:06:07 +0000 Subject: [PATCH 4/8] Update badges --- badges/reactions.svg | 2 +- 1 file changed, 1 insertion(+), 1 deletion(-) diff --git a/badges/reactions.svg b/badges/reactions.svg index 2051ac4..a478fef 100644 --- a/badges/reactions.svg +++ b/badges/reactions.svg @@ -1 +1 @@ -Reactions: 2376120Reactions2376120 \ No newline at end of file +Reactions: 2377347Reactions2377347 \ No newline at end of file From b5920ef9d55e67093c2952123ff623c9f9cfe074 Mon Sep 17 00:00:00 2001 From: Ben Deadman Date: Sun, 15 Mar 2026 22:50:47 +0000 Subject: [PATCH 5/8] Updated website in dataset description. --- data/1e/ord_dataset-1ec2807f02fa4beda27d2a81b86eb843.pb.gz | 4 ++-- 1 file changed, 2 insertions(+), 2 deletions(-) diff --git a/data/1e/ord_dataset-1ec2807f02fa4beda27d2a81b86eb843.pb.gz b/data/1e/ord_dataset-1ec2807f02fa4beda27d2a81b86eb843.pb.gz index 2c4d68a..4e7f4da 100644 --- a/data/1e/ord_dataset-1ec2807f02fa4beda27d2a81b86eb843.pb.gz +++ b/data/1e/ord_dataset-1ec2807f02fa4beda27d2a81b86eb843.pb.gz @@ -1,3 +1,3 @@ version https://git-lfs.github.com/spec/v1 -oid sha256:4ad15c3d5e56b95d26fba1aadc2761903aecae9b15b1793d2a52d52ec996ce18 -size 146316 +oid sha256:95199988c11f2f1c0762eee9460c18c5b790c135f0f3e4ac2fa0f7ba0ab00574 +size 146324 From 51893ec7b073f206fb495418e1d52bc53ec2d154 Mon Sep 17 00:00:00 2001 From: github-actions Date: Tue, 9 Jun 2026 15:37:22 +0000 Subject: [PATCH 6/8] Update badges --- badges/reactions.svg | 2 +- 1 file changed, 1 insertion(+), 1 deletion(-) diff --git a/badges/reactions.svg b/badges/reactions.svg index a478fef..5ea3e3e 100644 --- a/badges/reactions.svg +++ b/badges/reactions.svg @@ -1 +1 @@ -Reactions: 2377347Reactions2377347 \ No newline at end of file +Reactions: 2377347Reactions2377347 \ No newline at end of file From b6228f570c10a02aa7debdda7bd504967f58c388 Mon Sep 17 00:00:00 2001 From: Ben Deadman Date: Tue, 9 Jun 2026 16:41:39 +0100 Subject: [PATCH 7/8] Fix DOI field and is_desired_product flags Populate ReactionProvenance.doi with 10.48550/arXiv.2506.07619 across all 1,227 reactions (previously only set in publication_url). Set is_desired_product = True for Product 2 and Product 3 in all reactions. --- data/1e/ord_dataset-1ec2807f02fa4beda27d2a81b86eb843.pb.gz | 4 ++-- 1 file changed, 2 insertions(+), 2 deletions(-) diff --git a/data/1e/ord_dataset-1ec2807f02fa4beda27d2a81b86eb843.pb.gz b/data/1e/ord_dataset-1ec2807f02fa4beda27d2a81b86eb843.pb.gz index 4e7f4da..055b7f0 100644 --- a/data/1e/ord_dataset-1ec2807f02fa4beda27d2a81b86eb843.pb.gz +++ b/data/1e/ord_dataset-1ec2807f02fa4beda27d2a81b86eb843.pb.gz @@ -1,3 +1,3 @@ version https://git-lfs.github.com/spec/v1 -oid sha256:95199988c11f2f1c0762eee9460c18c5b790c135f0f3e4ac2fa0f7ba0ab00574 -size 146324 +oid sha256:3e533773a8bc0933f25d720e7a1ff97d18d05c58ba13cf762f57a14f8abe7d7b +size 146542 From 926e2dba2e18b93173f464d0d246a319beb88246 Mon Sep 17 00:00:00 2001 From: github-actions Date: Tue, 9 Jun 2026 15:44:56 +0000 Subject: [PATCH 8/8] Update submission --- data/1e/ord_dataset-1ec2807f02fa4beda27d2a81b86eb843.pb.gz | 4 ++-- 1 file changed, 2 insertions(+), 2 deletions(-) diff --git a/data/1e/ord_dataset-1ec2807f02fa4beda27d2a81b86eb843.pb.gz b/data/1e/ord_dataset-1ec2807f02fa4beda27d2a81b86eb843.pb.gz index 055b7f0..be09c92 100644 --- a/data/1e/ord_dataset-1ec2807f02fa4beda27d2a81b86eb843.pb.gz +++ b/data/1e/ord_dataset-1ec2807f02fa4beda27d2a81b86eb843.pb.gz @@ -1,3 +1,3 @@ version https://git-lfs.github.com/spec/v1 -oid sha256:3e533773a8bc0933f25d720e7a1ff97d18d05c58ba13cf762f57a14f8abe7d7b -size 146542 +oid sha256:a405946a81a5e90d94673ab3a61803f07bc3a541da6a3bb94265c1d9263ac3d0 +size 146536